CA3045224A1 - Pesticidal compounds - Google Patents
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- CA3045224A1 CA3045224A1 CA3045224A CA3045224A CA3045224A1 CA 3045224 A1 CA3045224 A1 CA 3045224A1 CA 3045224 A CA3045224 A CA 3045224A CA 3045224 A CA3045224 A CA 3045224A CA 3045224 A1 CA3045224 A1 CA 3045224A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/14—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
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Abstract
The present invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined according to the description. The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
Description
Pesticidal compounds Description Invertebrate pests and in particular insects, arachnids and nematodes destroy growing and har-vested crops and attack wooden dwelling and commercial structures, thereby causing large eco-nomic loss to the food supply and to property. Accordingly, there is an ongoing need for new agents for combating invertebrate pests.
Carbamoylated and thiocarbamoylated oxime derivatives are known for pesticidal use, for exam-ple, in patent publications WO 2016/156076, semi-carbazones and thiosemicarbazones derivatives are known for pesticidal use in patent publication WO 2016/116445.
Due to the ability of target pests to develop resistance to pesticidally-active agents, there is an on-going need to identify further compounds, which are suitable for combating invertebrate pests such as insects, arachnids and nematodes. Furthermore, there is a need for new compounds having a high pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes.
It is therefore an object of the present invention to identify and provide compounds, which exhibit a high pesticidal activity and have a broad activity spectrum against invertebrate pests.
It has been found that these objects can be achieved by substituted bicyclic compounds of for-mula I, as depicted and defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.
In a first aspect, the present invention relates to the compounds of formula I, Ar ArQLN'Ii G (I) Wherein A is N or CRA;
G is N or CRB;
R, RA, and RB are H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-C1-04-alkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, 0-Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C6-alkylen-NRbRc, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Q is NR2, 0, or S(0)m, wherein R2 is H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-al-kyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, 03-06-cycloalkoxy-C1-04-alkyl, which
Carbamoylated and thiocarbamoylated oxime derivatives are known for pesticidal use, for exam-ple, in patent publications WO 2016/156076, semi-carbazones and thiosemicarbazones derivatives are known for pesticidal use in patent publication WO 2016/116445.
Due to the ability of target pests to develop resistance to pesticidally-active agents, there is an on-going need to identify further compounds, which are suitable for combating invertebrate pests such as insects, arachnids and nematodes. Furthermore, there is a need for new compounds having a high pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes.
It is therefore an object of the present invention to identify and provide compounds, which exhibit a high pesticidal activity and have a broad activity spectrum against invertebrate pests.
It has been found that these objects can be achieved by substituted bicyclic compounds of for-mula I, as depicted and defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.
In a first aspect, the present invention relates to the compounds of formula I, Ar ArQLN'Ii G (I) Wherein A is N or CRA;
G is N or CRB;
R, RA, and RB are H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-C1-04-alkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, 0-Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C6-alkylen-NRbRc, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Q is NR2, 0, or S(0)m, wherein R2 is H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-al-kyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, 03-06-cycloalkoxy-C1-04-alkyl, which
2 are unsubstituted or substituted with halogen, C(0)-0Ra, Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C(0)-NRbRg, C(0)-Rd, SO2NRbRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RA', wherein RAr is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-01-04-alkyl, 03-06-cycloalkoxy-01-04-alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRg, Ci-C6-alkylen-NRbRc, 0-Ci-C6-alkylen-NRbRc, 01-06-alkylen-ON, NH-Ci-C6-alkylen-NRbRg, C(0)-NRbRg, C(0)-Rd, SO2NRbRg, or S(=0)mRe, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio, or benzyl, where the rings are un-substituted or substituted with Rf;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein is _CRxaRxb_, _0_, _5_, _NRxc_, _CRxa=CRxb_, _CRxaRxb_CRxaRxb_, _O-CRxaRxb-, -S-CRx-aRxb-, -N=CRxam _NRxc_CRxaRxbm _NRxg-C(=S)-, -N=C(S-Re)-, or Y is -CRYa=N-, wherein the N is bound to Z;
-NRYg-C(=0)-, wherein C(=0) is bound to Z; and -NRYc-C(=S)-, wherein C(=S) is bound to Z;
Z is a single bond;
-NRzc-C(=S)-, wherein C(=S) is bound to T;
-NR-C(=O), wherein C(=0) is bound to T;
-N=C(S-Rza)-, wherein T is bound to the carbon atom;
-0-C(=0)-, wherein T is bound to the carbon atom;
-0-C(=S)-, wherein T is bound to the carbon atom; and -NRzc-C(S-Rza)=, wherein T is bound to the carbon atom;
T is 0, N or N-RT;
R" is 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, Ci-C6-alkylen-NRbRg, 01-06-alkylen-ON, C(0)-NRbRc, C(0)-Rd, aryl, arylcarbonyl, aryl-aryloxy-C1-04-alkyl, hetaryl, carbonylhetaryl, hetaryl-01-04-alkyl, or he-taryloxy-01-04-alkyl, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-mem-bered bicyclic hetaryl;
R12 is a radical of the formula A1;
Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RA', wherein RAr is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-01-04-alkyl, 03-06-cycloalkoxy-01-04-alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRg, Ci-C6-alkylen-NRbRc, 0-Ci-C6-alkylen-NRbRc, 01-06-alkylen-ON, NH-Ci-C6-alkylen-NRbRg, C(0)-NRbRg, C(0)-Rd, SO2NRbRg, or S(=0)mRe, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio, or benzyl, where the rings are un-substituted or substituted with Rf;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein is _CRxaRxb_, _0_, _5_, _NRxc_, _CRxa=CRxb_, _CRxaRxb_CRxaRxb_, _O-CRxaRxb-, -S-CRx-aRxb-, -N=CRxam _NRxc_CRxaRxbm _NRxg-C(=S)-, -N=C(S-Re)-, or Y is -CRYa=N-, wherein the N is bound to Z;
-NRYg-C(=0)-, wherein C(=0) is bound to Z; and -NRYc-C(=S)-, wherein C(=S) is bound to Z;
Z is a single bond;
-NRzc-C(=S)-, wherein C(=S) is bound to T;
-NR-C(=O), wherein C(=0) is bound to T;
-N=C(S-Rza)-, wherein T is bound to the carbon atom;
-0-C(=0)-, wherein T is bound to the carbon atom;
-0-C(=S)-, wherein T is bound to the carbon atom; and -NRzc-C(S-Rza)=, wherein T is bound to the carbon atom;
T is 0, N or N-RT;
R" is 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, Ci-C6-alkylen-NRbRg, 01-06-alkylen-ON, C(0)-NRbRc, C(0)-Rd, aryl, arylcarbonyl, aryl-aryloxy-C1-04-alkyl, hetaryl, carbonylhetaryl, hetaryl-01-04-alkyl, or he-taryloxy-01-04-alkyl, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-mem-bered bicyclic hetaryl;
R12 is a radical of the formula A1;
3 R123 (Al) wherein # indicates the point of attachment to T;
R121, R122, R123 are H, halogen, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-al-kynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyloxy, 02-06-alkynyloxy, 01-06-alkoxy-01-04-alkoxy, 01-06-alkylcarbonlyoxy, 01-06-haloalkylcarbonlyoxy, 01-06-alkenylcarbonlyoxy, 03-06-cycloalkylcarbonlyoxy, or NRhRc, or one of R121, R122, R123 may also be oxo;
R124 is H, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyloxy;
and where Rxa, Rxb, Rya are H, halogen, 01-06-alkyl, 01-06-alkoxy, 01-06-haloalkyl, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, cycloalkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, Ci-C6-alkYlen-NRhRc, 01-06-alkylen-CN, C(0)-NRhRc, C(0)-Rd, SO2NRhRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rxc, RYc, Rzc are H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy, 03-06-cycloalkyl, C1-04-alkyl-03-06-cycloalkyl, or C1-04-alkyl-03-06-cyclo-alkoxy, which are unsubstituted or substituted with halogen;
RT is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, alkoxy, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, 03-06-cycloalkoxy-C1-04-alkyl, where the alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C(0)-NRhRc, C(0)-Rd, SO2NRhRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rzc together with RT if present, may form 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be replaced by a carbonyl or a C=N-R and/or wherein 1 or 2 CH2 moieties may be re-placed by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene are unsubstituted or substituted with Rh;
Rza is H, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, 03-06-cycloalkyl, 06-cycloalkoxy, or 01-04-alkyl-03-06-cycloalkyl, which are unsubstituted or substituted with halogen, Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C(0)-NRhRc, C(0)-Rd, phenyl, phenylcarbonyl and benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rza together with RT if present, may form 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be
R121, R122, R123 are H, halogen, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-al-kynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyloxy, 02-06-alkynyloxy, 01-06-alkoxy-01-04-alkoxy, 01-06-alkylcarbonlyoxy, 01-06-haloalkylcarbonlyoxy, 01-06-alkenylcarbonlyoxy, 03-06-cycloalkylcarbonlyoxy, or NRhRc, or one of R121, R122, R123 may also be oxo;
R124 is H, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyloxy;
and where Rxa, Rxb, Rya are H, halogen, 01-06-alkyl, 01-06-alkoxy, 01-06-haloalkyl, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, cycloalkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, Ci-C6-alkYlen-NRhRc, 01-06-alkylen-CN, C(0)-NRhRc, C(0)-Rd, SO2NRhRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rxc, RYc, Rzc are H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy, 03-06-cycloalkyl, C1-04-alkyl-03-06-cycloalkyl, or C1-04-alkyl-03-06-cyclo-alkoxy, which are unsubstituted or substituted with halogen;
RT is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, alkoxy, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, 03-06-cycloalkoxy-C1-04-alkyl, where the alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C(0)-NRhRc, C(0)-Rd, SO2NRhRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rzc together with RT if present, may form 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be replaced by a carbonyl or a C=N-R and/or wherein 1 or 2 CH2 moieties may be re-placed by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene are unsubstituted or substituted with Rh;
Rza is H, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, 03-06-cycloalkyl, 06-cycloalkoxy, or 01-04-alkyl-03-06-cycloalkyl, which are unsubstituted or substituted with halogen, Ci-C6-alkylen-NRbRc, 01-06-alkylen-CN, C(0)-NRhRc, C(0)-Rd, phenyl, phenylcarbonyl and benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rza together with RT if present, may form 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be
4 replaced by a carbonyl or a C=N-R and/or wherein 1 or 2 CH2 moieties may be re-placed by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh;
Ra, Rh and Rg are H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, 03-06-cycloalkoxy-C1-04-al-kyl, which are unsubstituted or substituted with halogen, 01-06-alkylen-ON, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rd is H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-al-kyl, 03-06-cycloalkyl, 03-06-cycloalky1-01-04-alkyl, 03-06-cycloalkoxy-01-04-alkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Re is 01-06-alkyl, 01-06-haloalkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rf is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-01-04-alkyl, 03-06-cycloalkoxyx-01-04-alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRhRg, Ci-C6-alkylen-NRbRc, 0-Ci-C6-alkylen-NRhRg, 01-06-alkylen-ON, NH-Ci-C6-alkylen-NRhRg, C(0)-NRhRg, C(0)-Rd, SO2NRhRg, or S(=0)mRe;
Rg is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-03-06-cycloalkoxy-C1-04-alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRhRg, Ci-C6-alkylen-NRhRg, 0-Ci-C6-alkylen-NRhRg, 01-06-alkylen-ON, NH-Ci-C6-alkylen-NRhRg, C(0)-NRhRg, C(0)-Rd, SO2NRhRg, or S(=0)mRe;
Rh halogen, OH, 01-06-alkyl, 03-06-cycloalkyl, or ON;
m is 0, 1, or 2;
and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
Moreover, the present invention also relates to processes and intermediates for preparing com-pounds of formula I and to active compound combinations comprising them.
Moreover, the present invention relates to agricultural or veterinary compositions comprising the compounds of formula I, and to the use of the compounds of formula I or compositions comprising them for combating or controlling invertebrate pests and/or for protecting crops, plants, plant propagation material and/or growing plants from attack and/or infestation by invertebrate pests. The present invention also re-lates to methods of applying the compounds of formula I. Furthermore, the present invention relates to seed comprising compounds of formula I. Wherein the compounds of formula I
includes N-ox-ides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
Ra, Rh and Rg are H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, 03-06-cycloalkoxy-C1-04-al-kyl, which are unsubstituted or substituted with halogen, 01-06-alkylen-ON, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rd is H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-al-kyl, 03-06-cycloalkyl, 03-06-cycloalky1-01-04-alkyl, 03-06-cycloalkoxy-01-04-alkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Re is 01-06-alkyl, 01-06-haloalkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rf is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-01-04-alkyl, 03-06-cycloalkoxyx-01-04-alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRhRg, Ci-C6-alkylen-NRbRc, 0-Ci-C6-alkylen-NRhRg, 01-06-alkylen-ON, NH-Ci-C6-alkylen-NRhRg, C(0)-NRhRg, C(0)-Rd, SO2NRhRg, or S(=0)mRe;
Rg is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, tri-01-06-alkylsilyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 01-06-alkoxy-01-04-alkoxy, 03-06-cycloalkyl, 03-06-cycloalkoxy, 03-06-cycloalkyl-03-06-cycloalkoxy-C1-04-alkyl, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRhRg, Ci-C6-alkylen-NRhRg, 0-Ci-C6-alkylen-NRhRg, 01-06-alkylen-ON, NH-Ci-C6-alkylen-NRhRg, C(0)-NRhRg, C(0)-Rd, SO2NRhRg, or S(=0)mRe;
Rh halogen, OH, 01-06-alkyl, 03-06-cycloalkyl, or ON;
m is 0, 1, or 2;
and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
Moreover, the present invention also relates to processes and intermediates for preparing com-pounds of formula I and to active compound combinations comprising them.
Moreover, the present invention relates to agricultural or veterinary compositions comprising the compounds of formula I, and to the use of the compounds of formula I or compositions comprising them for combating or controlling invertebrate pests and/or for protecting crops, plants, plant propagation material and/or growing plants from attack and/or infestation by invertebrate pests. The present invention also re-lates to methods of applying the compounds of formula I. Furthermore, the present invention relates to seed comprising compounds of formula I. Wherein the compounds of formula I
includes N-ox-ides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
5 With due modification of the starting compounds, the compounds of formula I
can be prepared by procedures as given in below schemes.
The compounds of the formula (I) can be prepared by the methods described herein after in below reactions and in the synthesis description of the preparation examples. In the reactions below, the radicals Ar, Q, G, R and R1, R2, Rxa, Rya, Ryz,Ryc, Rxc, R11, R12 are as defined above for formula (I), unless otherwise specified.
Compounds of formula (I) in which Z is a single bond or ¨NRzc¨C(=S)¨ or ¨NRzc¨C(=0)¨ or 0-C(=0)- or -0-C(=S)- and T is 0, N or N-RT denotes compounds of formula la and can be prepared in accordance with the methods described in the examples and by analogy to the methods de-scribed in WO 2011/017504 and as depicted in below reaction.
,R11 XC) Z¨T Z¨T
NH r I (El) 2 ArXN
Ar G Fea Ar G Rya (la) (II) Q N' In one embodiment of the above reaction, an aldehyde or ketone of the formula (II) is reacted with a compound of formula (El) wherein Z is ¨NRzc¨C(=S)¨ or¨NRzc¨C(=0)¨ and T is N, in the pres-ence or in the absence of a solvent. Suitable solvents are polar protic solvents, preferably Ethanol.
If the reaction is performed in the absence of a solvent, the compound of the formula (El) usually also act as solvent. Compounds of the formula (El) are commercially available or can be prepared according to Journal of Medicinal Chemistry, 2010, 53(8), 3048 or Bioorganic &
Medicinal Chemis-try Letters, 2009, 19(4), 1152-1154 or W02007003944.
According to another embodiment of the above reaction , an aldehyde or ketone compound of the formula (II) is first reacted with a hydrazine of the formula Rzcl\IHNH2 followed by the reaction with an isocyanate of the formula R11-NCO or with an isothiocyanate R11-NCS to yield a compound of the formula (la), wherein Z is -N(Rzc)-C(=0) or - N(Rzc)-C(=S) and T is N.
According to another embodiment of the above reaction , an aldehyde or ketone compound of the formula (II) is first reacted with a hydroxylamine followed by the reaction with a compounds R12-L, where Lisa suitable leaving group, such as halogen or activated OH. Thereby, a compound of the formula (la) will result, wherein Z is a single bond and T is 0.
According to another embodiment of the above reaction , an aldehyde or ketone compound of for-mula (II) is first reacted with a hydroxylamine followed by reaction with an isocyanate of the formula R11-NCO or with an isothiocyanate R11-NCS to yield a compound of the formula (la), wherein Z is --0-C(=0)- or -0-C(=S)-and T is N.
can be prepared by procedures as given in below schemes.
The compounds of the formula (I) can be prepared by the methods described herein after in below reactions and in the synthesis description of the preparation examples. In the reactions below, the radicals Ar, Q, G, R and R1, R2, Rxa, Rya, Ryz,Ryc, Rxc, R11, R12 are as defined above for formula (I), unless otherwise specified.
Compounds of formula (I) in which Z is a single bond or ¨NRzc¨C(=S)¨ or ¨NRzc¨C(=0)¨ or 0-C(=0)- or -0-C(=S)- and T is 0, N or N-RT denotes compounds of formula la and can be prepared in accordance with the methods described in the examples and by analogy to the methods de-scribed in WO 2011/017504 and as depicted in below reaction.
,R11 XC) Z¨T Z¨T
NH r I (El) 2 ArXN
Ar G Fea Ar G Rya (la) (II) Q N' In one embodiment of the above reaction, an aldehyde or ketone of the formula (II) is reacted with a compound of formula (El) wherein Z is ¨NRzc¨C(=S)¨ or¨NRzc¨C(=0)¨ and T is N, in the pres-ence or in the absence of a solvent. Suitable solvents are polar protic solvents, preferably Ethanol.
If the reaction is performed in the absence of a solvent, the compound of the formula (El) usually also act as solvent. Compounds of the formula (El) are commercially available or can be prepared according to Journal of Medicinal Chemistry, 2010, 53(8), 3048 or Bioorganic &
Medicinal Chemis-try Letters, 2009, 19(4), 1152-1154 or W02007003944.
According to another embodiment of the above reaction , an aldehyde or ketone compound of the formula (II) is first reacted with a hydrazine of the formula Rzcl\IHNH2 followed by the reaction with an isocyanate of the formula R11-NCO or with an isothiocyanate R11-NCS to yield a compound of the formula (la), wherein Z is -N(Rzc)-C(=0) or - N(Rzc)-C(=S) and T is N.
According to another embodiment of the above reaction , an aldehyde or ketone compound of the formula (II) is first reacted with a hydroxylamine followed by the reaction with a compounds R12-L, where Lisa suitable leaving group, such as halogen or activated OH. Thereby, a compound of the formula (la) will result, wherein Z is a single bond and T is 0.
According to another embodiment of the above reaction , an aldehyde or ketone compound of for-mula (II) is first reacted with a hydroxylamine followed by reaction with an isocyanate of the formula R11-NCO or with an isothiocyanate R11-NCS to yield a compound of the formula (la), wherein Z is --0-C(=0)- or -0-C(=S)-and T is N.
6 Compounds of formula (I) in which Z is ¨NRzc¨C(=S)¨ or ¨NRzc¨C(=0)¨, wherein C(=S) or C(=0) is bound to T and T is 0, N or N-RT, denotes compounds of formula lb and can be prepared as shown in reaction below by analogy to the method described in Synthesis, 2010, 2990-2966.
R
Z¨T
z (E2) Z¨T
ACIr)C NHRv' NCO
-11p. ACr)L0 Ar, G
Ar, G Ryz Q N' (111a) (lb) Q
y ArXy0 (IVa) (IVb) Ar,QG NHOH Ar, G N3 Q
According to the method depicted in the above reaction , an isocyanate compound of the formula (111a) is reacted with the compound of formula (E2) by methods known to a person skilled in the art.
The isocyanate of the formula (111a) may be obtained e.g. via Lossen rearrangement of the corre-sponding hydroxamic acid (IVa). The isocyanate of the formula (111a) may also be obtained via Cur-tius rearrangement of the corresponding azide of the formula (IVb), e.g. by analogy to the method described in WO 2014/204622. To this end, the hydroxamic acid is reacted with 1-pro-panephosphonic acid cyclic anhydride (T3P) in the presence of a base. The base is preferably N-methylmorpholine.
For converting compounds of formula (lb) in which RYz or Rzc is H into compounds (lb) in which RYz or Rxz is not H, compounds of formula (lb) in which RYz or Rzc is H can be reacted with compounds of formulae RYz¨Lg or Rzc¨Lg wherein RYz or Rzc is not H and Lg is a leaving group, such as a bro-mine, chlorine or iodine atom or a tosylate, mesylate or triflate, to yield compounds of formula (lb), wherein RYz or Rzc is different from H. The reaction is suitably carried out in the presence of a base such as sodium hydride or potassium hydride, suitably in a polar aprotic solvent such as N,N-dime-thylformamide, tetrahydrofuran, dioxane, acetonitrile, dimethylsulfoxide or pyridine, or mixtures of these solvents, in a temperature range of from 0 C and 100 C.
Compounds of formula (I) in which Z is a single bond and T is 0, N or N-RT, denotes compounds of formula lc and can be prepared as shown in reaction below by analogy to the methods described in WO 2011/017513.
Z¨T
X'1\1HRYc ArX'1\10 Ar,QG
(V) Ar, G RYc (Ic) Q N' In the above reaction, R11112 corresponds to radicals R11 or R12 respectively.
The reaction shown above can be performed by analogy to conventional methods of preparing carbamates. According
R
Z¨T
z (E2) Z¨T
ACIr)C NHRv' NCO
-11p. ACr)L0 Ar, G
Ar, G Ryz Q N' (111a) (lb) Q
y ArXy0 (IVa) (IVb) Ar,QG NHOH Ar, G N3 Q
According to the method depicted in the above reaction , an isocyanate compound of the formula (111a) is reacted with the compound of formula (E2) by methods known to a person skilled in the art.
The isocyanate of the formula (111a) may be obtained e.g. via Lossen rearrangement of the corre-sponding hydroxamic acid (IVa). The isocyanate of the formula (111a) may also be obtained via Cur-tius rearrangement of the corresponding azide of the formula (IVb), e.g. by analogy to the method described in WO 2014/204622. To this end, the hydroxamic acid is reacted with 1-pro-panephosphonic acid cyclic anhydride (T3P) in the presence of a base. The base is preferably N-methylmorpholine.
For converting compounds of formula (lb) in which RYz or Rzc is H into compounds (lb) in which RYz or Rxz is not H, compounds of formula (lb) in which RYz or Rzc is H can be reacted with compounds of formulae RYz¨Lg or Rzc¨Lg wherein RYz or Rzc is not H and Lg is a leaving group, such as a bro-mine, chlorine or iodine atom or a tosylate, mesylate or triflate, to yield compounds of formula (lb), wherein RYz or Rzc is different from H. The reaction is suitably carried out in the presence of a base such as sodium hydride or potassium hydride, suitably in a polar aprotic solvent such as N,N-dime-thylformamide, tetrahydrofuran, dioxane, acetonitrile, dimethylsulfoxide or pyridine, or mixtures of these solvents, in a temperature range of from 0 C and 100 C.
Compounds of formula (I) in which Z is a single bond and T is 0, N or N-RT, denotes compounds of formula lc and can be prepared as shown in reaction below by analogy to the methods described in WO 2011/017513.
Z¨T
X'1\1HRYc ArX'1\10 Ar,QG
(V) Ar, G RYc (Ic) Q N' In the above reaction, R11112 corresponds to radicals R11 or R12 respectively.
The reaction shown above can be performed by analogy to conventional methods of preparing carbamates. According
7 to a first embodiment, the amine of the formula (V) is converted into either an isocyanate or p-nitro-phenyl carbamate followed by treatment with an alcohol of the formula R11-0H
or R12-0H, respec-tively, in the presence of an organic or inorganic base. According to another embodiment, the com-pound of the formula (V) is reacted with a chloroformate of the formula R11/12-0-C(=0)-Cl. The chlo-roformate is prepared from the alcohols R11/120H by treatment with phosgene or triphosgene in the presence of a base, e.g. pyridine.
Compounds of formula (lc), in which Z is -N(R)-C(=O)- or -N(R)-C(=S)- can be prepared by analogy to the methods described in WO 2013/009791, especially in reactions described therein or by the methods described in US 2012/0202687.
Compounds of the formula (II) where X = -CRxa=cRxb_ or _CRxaRxb_CRxaRxb_ can be prepared by analogy to the methods described in the examples or prepared by the reactions shown in the fol-lowing reaction.
R R
ArHal (i) A X_ ,0 Iim=
Ar G Ar'QN'G RYa 'IC) 1\1' (11a) (II) In the above reaction, Hal is halogen, preferably chlorine or bromine, in particular, bromine. Suite-ble reaction conditions for performing the above reaction (reaction step (i)) is by a Cu-catalyzed cross-coupling reaction of (11a) with a alkenyl boronic acid or a alkenyl boronate ester using the methodology described in Journal of the American Chemical Society 2012, 134, 15165-15168. The alkenyl boronic acid or the alkenyl boronate ester can be prepared from the corresponding proper-gylic compounds.
Compounds of the formula (II) where X = -CRxa=CRxb- can also be prepared by reacting com-pounds of formula (I lb) with appropriate organophosphoranes (J. Heterocyclic Chem. 28: 1281 (1991)) or with appropriate organostannanes (Eur. Pat. Appl., 308736) (reaction step (ii), below re-action).
R R
CHO (H) A
I
-"...i'y AjrX,0 I r QN' Ar'G (11b) Ar G R'a 'Q Nr (II) Rxa = H
Compounds of the formula (II) where X = -c RxaRxb_c RxaRxb_ can be prepared from compounds of formula (II) where X = -CRxa=CRxb- by standard hydrogenation protocols known in organic chemis-try such as using hydrogen gas and a suitable metal catalyst as described in March's Advanced Or-ganic Chemistry 6th edition, Michael B. Smith and Jerry March.
Compounds of the formula (II) where X = -0_c RxaRxb_ or -S-CRxaRxb- can be prepared by anal-ogy to the methods descrbied in below reaction and in accordance with the methods described in the examples R R
ArOH/SH (iv) , 1 X_ ,0 ¨ Ar i Ar G Ar G Rya ' Q Nr (11c) 'Q Nr (II)
or R12-0H, respec-tively, in the presence of an organic or inorganic base. According to another embodiment, the com-pound of the formula (V) is reacted with a chloroformate of the formula R11/12-0-C(=0)-Cl. The chlo-roformate is prepared from the alcohols R11/120H by treatment with phosgene or triphosgene in the presence of a base, e.g. pyridine.
Compounds of formula (lc), in which Z is -N(R)-C(=O)- or -N(R)-C(=S)- can be prepared by analogy to the methods described in WO 2013/009791, especially in reactions described therein or by the methods described in US 2012/0202687.
Compounds of the formula (II) where X = -CRxa=cRxb_ or _CRxaRxb_CRxaRxb_ can be prepared by analogy to the methods described in the examples or prepared by the reactions shown in the fol-lowing reaction.
R R
ArHal (i) A X_ ,0 Iim=
Ar G Ar'QN'G RYa 'IC) 1\1' (11a) (II) In the above reaction, Hal is halogen, preferably chlorine or bromine, in particular, bromine. Suite-ble reaction conditions for performing the above reaction (reaction step (i)) is by a Cu-catalyzed cross-coupling reaction of (11a) with a alkenyl boronic acid or a alkenyl boronate ester using the methodology described in Journal of the American Chemical Society 2012, 134, 15165-15168. The alkenyl boronic acid or the alkenyl boronate ester can be prepared from the corresponding proper-gylic compounds.
Compounds of the formula (II) where X = -CRxa=CRxb- can also be prepared by reacting com-pounds of formula (I lb) with appropriate organophosphoranes (J. Heterocyclic Chem. 28: 1281 (1991)) or with appropriate organostannanes (Eur. Pat. Appl., 308736) (reaction step (ii), below re-action).
R R
CHO (H) A
I
-"...i'y AjrX,0 I r QN' Ar'G (11b) Ar G R'a 'Q Nr (II) Rxa = H
Compounds of the formula (II) where X = -c RxaRxb_c RxaRxb_ can be prepared from compounds of formula (II) where X = -CRxa=CRxb- by standard hydrogenation protocols known in organic chemis-try such as using hydrogen gas and a suitable metal catalyst as described in March's Advanced Or-ganic Chemistry 6th edition, Michael B. Smith and Jerry March.
Compounds of the formula (II) where X = -0_c RxaRxb_ or -S-CRxaRxb- can be prepared by anal-ogy to the methods descrbied in below reaction and in accordance with the methods described in the examples R R
ArOH/SH (iv) , 1 X_ ,0 ¨ Ar i Ar G Ar G Rya ' Q Nr (11c) 'Q Nr (II)
8 Compounds of the formula (II) where X = ¨0_c RxaRxb_ or ¨S¨CRxaRxb¨ can be prepared by first reacting compounds of formula (11c) with compounds of the formula Lg_cRxaRxb_c(0)Rya or Lg-CRx-aRxb¨C(0)0R" or Lg-CRxaRxb¨CN or Lg-CRxaRxb¨C(OR")2 with appropriate protecting groups and where Lg is a leaving group such as a bromine, chlorine or iodine atom or a tosylate, mesylate or triflate, to yield compounds of formula (11) (step (iv)). R" is alkyl, preferably methyl or ethyl. The re-sulting compounds can then be converted to compounds of the formula (II) by standard deprotec-tion methods - acidic hydrolysis for acetals as described in Greene's Protecting Groups in Organic Synthesis, reduction with reducing agents such as Diisobutylaluminium hydride for nitriles and es-ters as described in March's Advanced Organic Chemistry 6tb edition, Michael B. Smith and Jerry March.
In another embodiment of the reaction, compounds of the formula (11) where X =
¨0¨CRxaRxb¨ or ¨
S¨CRxaRxb¨ can be prepared by first reacting compounds of formula (11d) with compounds of the formula HO/HS-CRxaRxb_C(0)RYa or HO/HS-CRxaRxb¨C(0)0R" or HO/HS-CRxaRxb¨CN
with appro-priate protecting groups, by Cu or Pd catalysed reactions or uncatalysed reactions as described in W02011159839 or W02016027249 or U520070032485 and as depicted in below reaction.
Wherein -Hal is bromine, chlorine or iodine atom or a tosylate, mesylate or triflate; R" is a boronic acid or an ester of a boronic acid.
Hal/R"' (v) X 0 Ar G Ar G RYa N (11d) (II) Compounds of the formula (11) where X = ¨N=CRxa¨, ¨NRxc_c RxaRxbm _NRxb¨C(=S)¨, ¨N=C(S-Re)¨, or ¨NRxc¨C(=0)¨ can be prepared in accordance with the methods described in the exam-ples, from compounds of the formula (Ile) or can be prepared in accordance with below reaction.
R Rxc (vi) ArN H AJr I r ya Ar G Ar G R
Q N (Ile) Q N (II) Compounds of the formula (11) where X = ¨N=CR¨, ¨NRxc_c RxaRxbm _NRxb¨C(=S)¨, ¨N=C(S-Re)¨, or ¨NRxb¨C(=0)¨ can be prepared by first reacting compounds of formula (Ile) with com-pounds of the formula Lg-CRxaRxb_C(0)RYa or Lg-CRxaRxb¨C(0)0R" or Lg-CRxaRxb¨CN or H(OC)Rxa-C(0)RYa or Lg-(0C)Rxa-C(0)Rya or Lg-(0C)RxaCN with appropriate protecting groups and where Lg is a leaving group such as a bromine, chlorine or iodine atom or a tosylate, mesylate or triflate, to yield compounds of formula (11) (step (vi)). R" is alkyl, preferably methyl or ethyl as de-scribed in W02006065703 or WO 2011079305. The resulting compounds can then be converted to compounds of the formula (II) by methods described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March.
Compounds of the formula (11b), (11c), (11d) and (Ile) can be prepared by analogy to compounds prepared in the literature and in accordance with the compounds prepared in the examples. Usually compounds of the formula (11b), (11c), (11d) and (Ile) are prepared by the reactions shown in the fol-lowing reactions.
In another embodiment of the reaction, compounds of the formula (11) where X =
¨0¨CRxaRxb¨ or ¨
S¨CRxaRxb¨ can be prepared by first reacting compounds of formula (11d) with compounds of the formula HO/HS-CRxaRxb_C(0)RYa or HO/HS-CRxaRxb¨C(0)0R" or HO/HS-CRxaRxb¨CN
with appro-priate protecting groups, by Cu or Pd catalysed reactions or uncatalysed reactions as described in W02011159839 or W02016027249 or U520070032485 and as depicted in below reaction.
Wherein -Hal is bromine, chlorine or iodine atom or a tosylate, mesylate or triflate; R" is a boronic acid or an ester of a boronic acid.
Hal/R"' (v) X 0 Ar G Ar G RYa N (11d) (II) Compounds of the formula (11) where X = ¨N=CRxa¨, ¨NRxc_c RxaRxbm _NRxb¨C(=S)¨, ¨N=C(S-Re)¨, or ¨NRxc¨C(=0)¨ can be prepared in accordance with the methods described in the exam-ples, from compounds of the formula (Ile) or can be prepared in accordance with below reaction.
R Rxc (vi) ArN H AJr I r ya Ar G Ar G R
Q N (Ile) Q N (II) Compounds of the formula (11) where X = ¨N=CR¨, ¨NRxc_c RxaRxbm _NRxb¨C(=S)¨, ¨N=C(S-Re)¨, or ¨NRxb¨C(=0)¨ can be prepared by first reacting compounds of formula (Ile) with com-pounds of the formula Lg-CRxaRxb_C(0)RYa or Lg-CRxaRxb¨C(0)0R" or Lg-CRxaRxb¨CN or H(OC)Rxa-C(0)RYa or Lg-(0C)Rxa-C(0)Rya or Lg-(0C)RxaCN with appropriate protecting groups and where Lg is a leaving group such as a bromine, chlorine or iodine atom or a tosylate, mesylate or triflate, to yield compounds of formula (11) (step (vi)). R" is alkyl, preferably methyl or ethyl as de-scribed in W02006065703 or WO 2011079305. The resulting compounds can then be converted to compounds of the formula (II) by methods described in March's Advanced Organic Chemistry 6th edition, Michael B. Smith and Jerry March.
Compounds of the formula (11b), (11c), (11d) and (Ile) can be prepared by analogy to compounds prepared in the literature and in accordance with the compounds prepared in the examples. Usually compounds of the formula (11b), (11c), (11d) and (Ile) are prepared by the reactions shown in the fol-lowing reactions.
9 R R R
A jHal COOR"
I NO Ar, ArCHO
Ar'QNrG -1" I ' (viii) 1 Ar G ->
õ
'Q N-- fro-, ..õ1-... G
Q N' (11d) (11h) (11b) RXa = H
R R R
Hal Ar I (ix) A A
i CH2 (x) iCHO
Ar, G A,QN-6 ' r -1111.
Q N Ar,Q.N'G
(11d) (11f) (11b) RXa = H
R
R
lr Hal R
A
I (xi) A jrCN
Ar CHO
Ar'QNI'G -II. (Xii) 1 Ar,QNI'G -am' Ar,,J G
QNr (11d) (11g) (11b) RXa = H
R
Hal R
A
1 (xiii) ANHRxc Ar'Ql\rG -3Iw i Ar,QNI'G
(11d) (Ile) R R R
ArHal ArOH
I (xiv) ArR I (xv) I
Ar, G -I" At-, G
Q N' Q N' -311. Ar, G
Q Nr (11d) (11d) (11c) R R
ArHal CHO
1 (xvi) Ar, Ar' QNI'G -II' I G
' Ar,QN' (11d) (11b) Rxa = H
In the above reactions, -Hal is bromine, chlorine or iodine atom or a tosylate, mesylate or triflate;
R¨ is a boronic acid of an ester of a boronic acid.
Suitable reaction conditions for performing the preparation of the cyanide compound of the for-mula (11g) (reaction step (x)) by a Pd-catalyzed aromatic cyanation reaction of an aryl bromide of the formula (11d) with an alkalimetal cyanide, preferably NaCN, can be taken from Journal of the American Chemical Society, 133 (28), 10999-11005; 2011.The reduction of a cyanide compound (11g) to an aldehyde compound (11b) shown in step (xii) of the above reactions can be performed with a metal alkoxyaluminum hydride. Suitable alkoxyaluminum hydrides are lithium alkoxyalumi-num hydrides and sodium alkoxyaluminum hydrides, e.g. Na[A1(0C2H5)3H].
Suitable reaction condi-tions for step (viii) of the above reaction can be taken from Organic Reactions (Hooboken, NJ, United States), pp 36, 1988. The conversion of the aryl bromide (11d) into the ester compound (11h) is shown in reaction step (vii) of the above reaction. Suitable reaction conditions for this palladium-catalysed reaction can be taken from Journal of Medicinal Chemistry, 52 (22), 7258-7272; 2009.
Suitable reaction conditions for performing step (viii) of the above reaction can be taken from Syn-5 lett, (6), 869-872; 2006. Suitable reaction conditions for performing the reaction step (ix) of the above reaction can be taken from Journal of the American Chemical Society, 124(22), 6343-6348, 2002. Suitable reaction conditions for performing the reaction step (x) of the above reaction can be taken from European Journal of Medicinal Chemistry, 49, 310-323; 2012.
Compounds of the for-mula (11b) can also made from compounds of formula (11d) by reaction with as strong base like for
A jHal COOR"
I NO Ar, ArCHO
Ar'QNrG -1" I ' (viii) 1 Ar G ->
õ
'Q N-- fro-, ..õ1-... G
Q N' (11d) (11h) (11b) RXa = H
R R R
Hal Ar I (ix) A A
i CH2 (x) iCHO
Ar, G A,QN-6 ' r -1111.
Q N Ar,Q.N'G
(11d) (11f) (11b) RXa = H
R
R
lr Hal R
A
I (xi) A jrCN
Ar CHO
Ar'QNI'G -II. (Xii) 1 Ar,QNI'G -am' Ar,,J G
QNr (11d) (11g) (11b) RXa = H
R
Hal R
A
1 (xiii) ANHRxc Ar'Ql\rG -3Iw i Ar,QNI'G
(11d) (Ile) R R R
ArHal ArOH
I (xiv) ArR I (xv) I
Ar, G -I" At-, G
Q N' Q N' -311. Ar, G
Q Nr (11d) (11d) (11c) R R
ArHal CHO
1 (xvi) Ar, Ar' QNI'G -II' I G
' Ar,QN' (11d) (11b) Rxa = H
In the above reactions, -Hal is bromine, chlorine or iodine atom or a tosylate, mesylate or triflate;
R¨ is a boronic acid of an ester of a boronic acid.
Suitable reaction conditions for performing the preparation of the cyanide compound of the for-mula (11g) (reaction step (x)) by a Pd-catalyzed aromatic cyanation reaction of an aryl bromide of the formula (11d) with an alkalimetal cyanide, preferably NaCN, can be taken from Journal of the American Chemical Society, 133 (28), 10999-11005; 2011.The reduction of a cyanide compound (11g) to an aldehyde compound (11b) shown in step (xii) of the above reactions can be performed with a metal alkoxyaluminum hydride. Suitable alkoxyaluminum hydrides are lithium alkoxyalumi-num hydrides and sodium alkoxyaluminum hydrides, e.g. Na[A1(0C2H5)3H].
Suitable reaction condi-tions for step (viii) of the above reaction can be taken from Organic Reactions (Hooboken, NJ, United States), pp 36, 1988. The conversion of the aryl bromide (11d) into the ester compound (11h) is shown in reaction step (vii) of the above reaction. Suitable reaction conditions for this palladium-catalysed reaction can be taken from Journal of Medicinal Chemistry, 52 (22), 7258-7272; 2009.
Suitable reaction conditions for performing step (viii) of the above reaction can be taken from Syn-5 lett, (6), 869-872; 2006. Suitable reaction conditions for performing the reaction step (ix) of the above reaction can be taken from Journal of the American Chemical Society, 124(22), 6343-6348, 2002. Suitable reaction conditions for performing the reaction step (x) of the above reaction can be taken from European Journal of Medicinal Chemistry, 49, 310-323; 2012.
Compounds of the for-mula (11b) can also made from compounds of formula (11d) by reaction with as strong base like for
10 example n-butyl lithium and with an electrophile, for example N,N-Dimethylformamide as shown in reaction step (xvi), of the above reaction.
Compounds of the formula (Ile) (reaction step (xiii) of the above reaction) can be prepared by re-acting compounds of the formula (11d) with ammonia or amines of the formula RxcNH2 in the pres-ence of a metal catalyst or its salts, preferably copper or its salts as described in Chem. Commun., 2009, 3035-3037. Compounds of formula (11c) can be made from compounds of formula (11d) by oxi-dation with various oxidation reagents for example, hydrogen peroxide as described in Bioorganic and Medicinal chemistry letters, 2013, 23, 4705-4712. Compounds of formula (11d') can be made from compounds of the formula (11d) by reacting with a Palladium (II) catalyzed reaction with pinacol boronates or by reaction with a base such as n-Butyl lithium and trialkylborates as described in Bioorganic and medicinal chemistry letters, 2013, 23, 4705-4712.
Compounds of the formula (11d) can be prepared from compounds of formula (11h) as per below reaction.
ArHal (xi) ArHal Hal NG' (11h) ArG (11d) In the above reaction, Hal' can be fluorine, chlorine, bromine or iodine, preferably chlorine or to-sylate, mesylate or triflate. Hal can be chlorine, bromine or iodine, preferably bromine or tosylate, mesylate or triflate. Compounds of the formula (11d) can be prepared from compounds of formula (11h) by reacting with compounds of the formula Ar-OH or Ar-NHR2 by heating in a polar protic or aprotic solvents in an acidic, basic or neutral conditions as described in W02010129053, W02007146824 or Chemical Communications, 2014, 50, 1465.
Compounds of formula (11d) can also be prepared from compounds of formula (Ili) by reaction with aromatic halogen compounds or aromatic boronic acids or their esters under Cu(I), Cu(II) or Pd(II) catalysed conditions as described in WO 2007056075 or W02002066480 or by using methods de-scribed in Organic Letters 2009,11, 2514 as shown in below reaction.
AJHal (xviii) Hal HO/NH2 Ar,c)Li\rG (11d) 1VG (111)
Compounds of the formula (Ile) (reaction step (xiii) of the above reaction) can be prepared by re-acting compounds of the formula (11d) with ammonia or amines of the formula RxcNH2 in the pres-ence of a metal catalyst or its salts, preferably copper or its salts as described in Chem. Commun., 2009, 3035-3037. Compounds of formula (11c) can be made from compounds of formula (11d) by oxi-dation with various oxidation reagents for example, hydrogen peroxide as described in Bioorganic and Medicinal chemistry letters, 2013, 23, 4705-4712. Compounds of formula (11d') can be made from compounds of the formula (11d) by reacting with a Palladium (II) catalyzed reaction with pinacol boronates or by reaction with a base such as n-Butyl lithium and trialkylborates as described in Bioorganic and medicinal chemistry letters, 2013, 23, 4705-4712.
Compounds of the formula (11d) can be prepared from compounds of formula (11h) as per below reaction.
ArHal (xi) ArHal Hal NG' (11h) ArG (11d) In the above reaction, Hal' can be fluorine, chlorine, bromine or iodine, preferably chlorine or to-sylate, mesylate or triflate. Hal can be chlorine, bromine or iodine, preferably bromine or tosylate, mesylate or triflate. Compounds of the formula (11d) can be prepared from compounds of formula (11h) by reacting with compounds of the formula Ar-OH or Ar-NHR2 by heating in a polar protic or aprotic solvents in an acidic, basic or neutral conditions as described in W02010129053, W02007146824 or Chemical Communications, 2014, 50, 1465.
Compounds of formula (11d) can also be prepared from compounds of formula (Ili) by reaction with aromatic halogen compounds or aromatic boronic acids or their esters under Cu(I), Cu(II) or Pd(II) catalysed conditions as described in WO 2007056075 or W02002066480 or by using methods de-scribed in Organic Letters 2009,11, 2514 as shown in below reaction.
AJHal (xviii) Hal HO/NH2 Ar,c)Li\rG (11d) 1VG (111)
11 Compounds of the formula (11h) and (Ili) can be obtained from commercial sources or alternatively be prepared by using methods given in US 20050222228 and Journal of Organic Chemistry, 2002, 77(16), 6908, respectively.
Individual compounds of formula I can also be prepared by derivatisation of other compounds of formula I or the intermediates thereof.
If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during appli-cation (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.
Unless otherwise indicated, the term "compound(s) according to the invention"
or "compound(s) of the invention" or "compound(s) of formula (I)", refers to the compounds of formula I.
The term "compound(s) according to the invention", or "compounds of formula!"
comprises the compound(s) as defined herein as well as a stereoisomer, salt, tautomer or N-oxide thereof. The term "compound(s) of the present invention" is to be understood as equivalent to the term "com-pound(s) according to the invention", therefore also comprising a stereoisomer, salt, tautomer or N-oxide thereof.
The term "composition(s) according to the invention" or "composition(s) of the present invention"
encompasses composition(s) comprising at least one compound of formula I
according to the in-vention as defined above. The compositions of the invention are preferably agricultural or veterinary compositions.
Depending on the substitution pattern, the compounds according to the invention may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastere-omers. The invention provides both the single pure enantiomers or pure diastereomers of the com-pounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the invention or their mix-tures. Suitable compounds according to the invention also include all possible geometrical stereoi-somers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers). The pre-sent invention relates to every possible stereoisomer of the compounds of formula 1, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
The compounds according to the invention may be amorphous or may exist in one or more differ-ent crystalline states (polymorphs) which may have different macroscopic properties such as stabil-
Individual compounds of formula I can also be prepared by derivatisation of other compounds of formula I or the intermediates thereof.
If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during appli-cation (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.
Unless otherwise indicated, the term "compound(s) according to the invention"
or "compound(s) of the invention" or "compound(s) of formula (I)", refers to the compounds of formula I.
The term "compound(s) according to the invention", or "compounds of formula!"
comprises the compound(s) as defined herein as well as a stereoisomer, salt, tautomer or N-oxide thereof. The term "compound(s) of the present invention" is to be understood as equivalent to the term "com-pound(s) according to the invention", therefore also comprising a stereoisomer, salt, tautomer or N-oxide thereof.
The term "composition(s) according to the invention" or "composition(s) of the present invention"
encompasses composition(s) comprising at least one compound of formula I
according to the in-vention as defined above. The compositions of the invention are preferably agricultural or veterinary compositions.
Depending on the substitution pattern, the compounds according to the invention may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastere-omers. The invention provides both the single pure enantiomers or pure diastereomers of the com-pounds according to the invention, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds according to the invention or their mix-tures. Suitable compounds according to the invention also include all possible geometrical stereoi-somers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers). The pre-sent invention relates to every possible stereoisomer of the compounds of formula 1, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
The compounds according to the invention may be amorphous or may exist in one or more differ-ent crystalline states (polymorphs) which may have different macroscopic properties such as stabil-
12 ity or show different biological properties such as activities. The present invention relates to amor-phous and crystalline compounds according to the invention, mixtures of different crystalline states of the respective compounds according to the invention, as well as amorphous or crystalline salts thereof.
The term "tautomers" encompasses isomers, which are derived from the compounds of formula I
by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
The term "stereoisomers" encompasses both optical isomers, such as enantiomers or diastere-omers, the latter existing due to more than one center of chirality in the molecule, as well as geo-metrical isomers (cis/trans isomers).
Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R1. The in-vention provides both the pure enantiomers or diastereomers and their mixtures and the use ac-cording to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
The term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of an N-hetero-cycle, e.g. a pyridine or pyrimidine ring present in Ar or R11, or an imino-nitrogen present in central tricyclic core, with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
The person skilled in the art knows if and in which positions compounds of the present invention may form N-oxides.
Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
Suitable agriculturally or veterinarily acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, which are known and accepted in the art for the formation of salts for agricultural or veterinary use respectively, and do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alka-line earth metals, preferably calcium, magnesium and barium, and of the transition metals, prefera-bly manganese, copper, zinc and iron, and also ammonium (NH4) and substituted ammonium in which one to four of the hydrogen atoms are replaced by 01-04-alkyl, 01-04-hydroxyalkyl, 01-04-alkoxy, 01-04-alkoxy-01-04-alkyl, hydroxy-01-04-alkoxy-01-04-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium,
The term "tautomers" encompasses isomers, which are derived from the compounds of formula I
by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
The term "stereoisomers" encompasses both optical isomers, such as enantiomers or diastere-omers, the latter existing due to more than one center of chirality in the molecule, as well as geo-metrical isomers (cis/trans isomers).
Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R1. The in-vention provides both the pure enantiomers or diastereomers and their mixtures and the use ac-cording to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
The term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of an N-hetero-cycle, e.g. a pyridine or pyrimidine ring present in Ar or R11, or an imino-nitrogen present in central tricyclic core, with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
The person skilled in the art knows if and in which positions compounds of the present invention may form N-oxides.
Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
Suitable agriculturally or veterinarily acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, which are known and accepted in the art for the formation of salts for agricultural or veterinary use respectively, and do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alka-line earth metals, preferably calcium, magnesium and barium, and of the transition metals, prefera-bly manganese, copper, zinc and iron, and also ammonium (NH4) and substituted ammonium in which one to four of the hydrogen atoms are replaced by 01-04-alkyl, 01-04-hydroxyalkyl, 01-04-alkoxy, 01-04-alkoxy-01-04-alkyl, hydroxy-01-04-alkoxy-01-04-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium,
13 diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabu-tylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxy-ethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium, furthermore phospho-nium ions, sulfonium ions, preferably tri(01-04-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-04-alkyl)sulfoxonium. Suitable acid addition veterinarily acceptable salts, e.g. formed by com-pounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inor-ganic acids, for example hydrochlorides, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sul-fenic acid, methane sulfonic acid, and succinic acid.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sul-fate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, car-bonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of 01-04-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The term "invertebrate pest" as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded ani-mals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
The plant propagation materials may be treated prophylactically with a plant protection compound either at or before plant-ing or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
The term "plants" comprises any types of plants including "modified plants"
and in particular "culti-vated plants".
The term "modified plants" refers to any wild type species or related species or related genera of a cultivated plant.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech prod-ucts on the market or in development (cf.
http://www.bio.org/speeches/pubs/er/agri_products.asp).
Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational mod-ification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sul-fate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, car-bonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of 01-04-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The term "invertebrate pest" as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded ani-mals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
The plant propagation materials may be treated prophylactically with a plant protection compound either at or before plant-ing or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
The term "plants" comprises any types of plants including "modified plants"
and in particular "culti-vated plants".
The term "modified plants" refers to any wild type species or related species or related genera of a cultivated plant.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech prod-ucts on the market or in development (cf.
http://www.bio.org/speeches/pubs/er/agri_products.asp).
Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational mod-ification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as
14 prenylated, acetylated or farnesylated moieties or PEG moieties.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibi-tors or phytoene desaturase (PDS) inhibittors; acetolactate synthase (ALS) inhibitors such as sul-fonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;
protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA
carboxylase (ACCase) inhibi-tors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding .. or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbi-cides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS
inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286;
.. 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J.
Agricult. Res. 58, 2007, 708;
Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been ren-dered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
imazamox, or ExpressSun sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g.
tribenuron. Genetic .. engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are com-mercially available under the trade names RoundupReady (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance (imidazolinone tolerant, BASF SE, Germany) and LibertyLink (glufosinate-tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA
techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as 5-endotoxins, e.
g. CrylA(b), CrylA(c), CryIF, CryIF(a2), CryllA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e. g.
VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhab-dus spp. or Xenorhabdusspp.; toxins produced by animals, such as scorpion toxins, arachnid tox-ins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomy-cetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inacti-vating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxi-dases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of so-dium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin re-ceptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the pre-sent invention these insecticidal proteins or toxins are to be understood expressly also as pre-tox-ins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO
03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These in-5 secticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nema-toda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such 10 as YieldGard (corn cultivars producing the Cry1Ab toxin), YieldGard Plus (corn cultivars produc-ing Cry1Ab and Cry3Bb1 toxins), Starlink (corn cultivars producing the Cry9c toxin), Herculex RW
(corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransfer-ase [PAT]); NuCOTN 33B (cotton cultivars producing the Cry1Ac toxin), Bollgard I (cotton culti-vars producing the Cry1Ac toxin), Bollgard ll (cotton cultivars producing Cry1Ac and Cry2Ab2 tox-
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibi-tors or phytoene desaturase (PDS) inhibittors; acetolactate synthase (ALS) inhibitors such as sul-fonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;
protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA
carboxylase (ACCase) inhibi-tors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding .. or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbi-cides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS
inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286;
.. 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J.
Agricult. Res. 58, 2007, 708;
Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been ren-dered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
imazamox, or ExpressSun sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g.
tribenuron. Genetic .. engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are com-mercially available under the trade names RoundupReady (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance (imidazolinone tolerant, BASF SE, Germany) and LibertyLink (glufosinate-tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA
techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as 5-endotoxins, e.
g. CrylA(b), CrylA(c), CryIF, CryIF(a2), CryllA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e. g.
VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhab-dus spp. or Xenorhabdusspp.; toxins produced by animals, such as scorpion toxins, arachnid tox-ins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomy-cetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inacti-vating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxi-dases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of so-dium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin re-ceptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the pre-sent invention these insecticidal proteins or toxins are to be understood expressly also as pre-tox-ins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO
03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These in-5 secticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nema-toda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such 10 as YieldGard (corn cultivars producing the Cry1Ab toxin), YieldGard Plus (corn cultivars produc-ing Cry1Ab and Cry3Bb1 toxins), Starlink (corn cultivars producing the Cry9c toxin), Herculex RW
(corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransfer-ase [PAT]); NuCOTN 33B (cotton cultivars producing the Cry1Ac toxin), Bollgard I (cotton culti-vars producing the Cry1Ac toxin), Bollgard ll (cotton cultivars producing Cry1Ac and Cry2Ab2 tox-
15 ins); VIPCOT (cotton cultivars producing a VIP-toxin); NewLeaf (potato cultivars producing the Cry3A toxin); Bt-Xtra , NatureGard , KnockOut , BiteGard , Protecta , Bt11 (e.
g. Agrisure CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the Cry1Ab toxin and PAT
enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn culti-vars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA
techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacte-rial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato culti-vars, which express resistance genes acting against Phytophthora Infestans derived from the mexi-can wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthe-sizing these proteins with increased resistance against bacteria such as Erwinta amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA
techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve hu-man or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty ac-ids or unsaturated omega-9 fatty acids (e. g. Nexera rape, DOW Agro Sciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a
g. Agrisure CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the Cry1Ab toxin and PAT
enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn culti-vars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA
techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacte-rial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato culti-vars, which express resistance genes acting against Phytophthora Infestans derived from the mexi-can wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthe-sizing these proteins with increased resistance against bacteria such as Erwinta amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA
techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve hu-man or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty ac-ids or unsaturated omega-9 fatty acids (e. g. Nexera rape, DOW Agro Sciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a
16 modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora potato, BASF SE, Germany).
The organic moieties mentioned in the above definitions of the variables are -like the term halo-.. gen - collective terms for individual listings of the individual members.
The prefix On-Cm indicates in each case the possible number of carbon atoms in the group.
The term halogen denotes in each case F, Br, Cl or 1, in particular F, Cl or Br.
The term "alkyl" as used herein and in the alkyl moieties of alkoxy, alkylthio, and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 ("C1-02-alkyl"), 1 to 3 ("Ci-.. 03-alkyl"),1 to 4 ("Ci-04-alkyl") or Ito 6 ("Ci-06-alkyl") carbon atoms. 01-02-Alkyl is CH3or 02H5.
03-Alkyl is additionally propyl and isopropyl. Ci-04-Alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl (tert-butyl). 01-06-Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dime-thylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethy1-1-methylpropyl, or 1-ethy1-2-methylpropyl.
The term "haloalkyl" as used herein, which is also expressed as "alkyl which is partially or fully halogenated", refers to straight-chain or branched alkyl groups having 1 to 2 ("Ci-02-haloal-kyr), 1 to 3 ("C1-03-haloalkyl"), 1 to 4 ("Ci-04-haloalkyl") or 1 to 6 ("Ci-06-haloalkyl") carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular 01-02-haloalkyl, such as chloromethyl, bromome-thyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluorome-thyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoro-ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di-chloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl. 01-03-haloalkyl is additionally, for ex-ample, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and the like. Examples for 01-04-haloalkyl are, apart those mentioned for 01-03-haloal-kyl, 4-chlorobutyl and the like.
The term "alkylene" (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety. Alkylene has preferably 1 to 6 carbon at-oms (Ci-06-alkylene), 2 to 6 carbon atoms (02-06-alkylene), in particular 1 to 4 carbon atoms (Ci-C4-alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene). Examples of alkylene are methylene (CH2), 1,1-ethandiyl, 1,2-ethandiyl, 1,3-propandiyl, 1,2-propandiyl, 2,2-propandiyl, 1,4-butandiyl, 1,2-bu-tandiyl, 1,3-butandiyl, 2,3-butandiyl, 2,2-butandiyl, 1,5-pentandiyl, 2,2-dimethylpropan-1,3-diyl, 1,3-dimethy1-1,3-propandiyl, 1,6-hexandiy1 etc.
The term "alkenyl" as used herein refers to monounsaturated straight-chain or branched hy-drocarbon radicals having 2 to 3 ("02-03-alkenyl"), 2 to 4 ("02-04-alkenyl") or 2 to 6 ("02-06-alkenyl)
The organic moieties mentioned in the above definitions of the variables are -like the term halo-.. gen - collective terms for individual listings of the individual members.
The prefix On-Cm indicates in each case the possible number of carbon atoms in the group.
The term halogen denotes in each case F, Br, Cl or 1, in particular F, Cl or Br.
The term "alkyl" as used herein and in the alkyl moieties of alkoxy, alkylthio, and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 ("C1-02-alkyl"), 1 to 3 ("Ci-.. 03-alkyl"),1 to 4 ("Ci-04-alkyl") or Ito 6 ("Ci-06-alkyl") carbon atoms. 01-02-Alkyl is CH3or 02H5.
03-Alkyl is additionally propyl and isopropyl. Ci-04-Alkyl is additionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl (tert-butyl). 01-06-Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dime-thylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethy1-1-methylpropyl, or 1-ethy1-2-methylpropyl.
The term "haloalkyl" as used herein, which is also expressed as "alkyl which is partially or fully halogenated", refers to straight-chain or branched alkyl groups having 1 to 2 ("Ci-02-haloal-kyr), 1 to 3 ("C1-03-haloalkyl"), 1 to 4 ("Ci-04-haloalkyl") or 1 to 6 ("Ci-06-haloalkyl") carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular 01-02-haloalkyl, such as chloromethyl, bromome-thyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluorome-thyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoro-ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di-chloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl. 01-03-haloalkyl is additionally, for ex-ample, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and the like. Examples for 01-04-haloalkyl are, apart those mentioned for 01-03-haloal-kyl, 4-chlorobutyl and the like.
The term "alkylene" (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety. Alkylene has preferably 1 to 6 carbon at-oms (Ci-06-alkylene), 2 to 6 carbon atoms (02-06-alkylene), in particular 1 to 4 carbon atoms (Ci-C4-alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene). Examples of alkylene are methylene (CH2), 1,1-ethandiyl, 1,2-ethandiyl, 1,3-propandiyl, 1,2-propandiyl, 2,2-propandiyl, 1,4-butandiyl, 1,2-bu-tandiyl, 1,3-butandiyl, 2,3-butandiyl, 2,2-butandiyl, 1,5-pentandiyl, 2,2-dimethylpropan-1,3-diyl, 1,3-dimethy1-1,3-propandiyl, 1,6-hexandiy1 etc.
The term "alkenyl" as used herein refers to monounsaturated straight-chain or branched hy-drocarbon radicals having 2 to 3 ("02-03-alkenyl"), 2 to 4 ("02-04-alkenyl") or 2 to 6 ("02-06-alkenyl)
17 carbon atoms and a double bond in any position, for example 02-03-alkenyl, such as ethenyl, 1-pro-penyl, 2-propenyl or 1-methylethenyl; 02-04-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; 02-06-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-meth-ylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methy1-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methy1-1-butenyl, 3-methy1-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethy1-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethy1-2-propenyl, 1-ethyl-1-propenyl, 1-ethy1-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methy1-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methy1-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methy1-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethy1-2-butenyl, 1,1-dimethy1-3-butenyl, 1,2-dimethy1-1-butenyl, 1,2-dimethy1-2-butenyl, 1,2-dimethy1-3-bu-tenyl, 1,3-dimethy1-1-butenyl, 1,3-dimethy1-2-butenyl, 1,3-dimethy1-3-butenyl, 2,2-dimethy1-3-bu-tenyl, 2,3-dimethy1-1-butenyl, 2,3-dimethy1-2-butenyl, 2,3-dimethy1-3-butenyl, 3,3-dimethy1-1-bu-tenyl, 3,3-dimethy1-2-butenyl, 1-ethyl-1-butenyl, 1-ethy1-2-butenyl, 1-ethy1-3-butenyl, 2-ethy1-1-bu-tenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethy1-2-propenyl, 1-ethyl-1-methy1-2-propenyl, 1-ethy1-2-methy1-1-propenyl, 1-ethy1-2-methy1-2-propenyl and the like.
The term "alkynyl" as used herein refers to straight-chain or branched hydrocarbon groups having 2 to 3 ("02-03-alkynyl"), 2 to 4 ("02-04-alkynyl") or 2 to 6 ("02-06-alkynyl") carbon atoms and one or two triple bonds in any position, for example 02-03-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; 02-04-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, 02-06-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methy1-1-butynyl, 1,1-dimethy1-2-propynyl, 1-ethy1-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-me-thy1-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methy1-1-pentynyl, 3-methyl-4-pentynyl, 4-methy1-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethy1-2-butynyl, 1,1-dimethy1-3-butynyl, 1,2-dimethy1-3-butynyl, 2,2-dimethy1-3-butynyl, 3,3-dimethy1-1-butynyl, 1-ethy1-2-butynyl, 1-ethy1-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methy1-2-propynyl and the like;
The term "cycloalkyl" as used herein refers to mono- or bi- or polycyclic saturated hydrocar-bon radicals having in particular 3 to 6 ("03-06-cycloalkyl") or 3 to 5 ("03-05-cycloalkyl") or 3 to 4 ("03-04-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Examples of monocy-clic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicy-clo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
The term "alkynyl" as used herein refers to straight-chain or branched hydrocarbon groups having 2 to 3 ("02-03-alkynyl"), 2 to 4 ("02-04-alkynyl") or 2 to 6 ("02-06-alkynyl") carbon atoms and one or two triple bonds in any position, for example 02-03-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; 02-04-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, 02-06-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methy1-1-butynyl, 1,1-dimethy1-2-propynyl, 1-ethy1-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-me-thy1-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methy1-1-pentynyl, 3-methyl-4-pentynyl, 4-methy1-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethy1-2-butynyl, 1,1-dimethy1-3-butynyl, 1,2-dimethy1-3-butynyl, 2,2-dimethy1-3-butynyl, 3,3-dimethy1-1-butynyl, 1-ethy1-2-butynyl, 1-ethy1-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methy1-2-propynyl and the like;
The term "cycloalkyl" as used herein refers to mono- or bi- or polycyclic saturated hydrocar-bon radicals having in particular 3 to 6 ("03-06-cycloalkyl") or 3 to 5 ("03-05-cycloalkyl") or 3 to 4 ("03-04-cycloalkyl") carbon atoms. Examples of monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examples of monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Examples of monocy-clic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicy-clo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
18 The term "cycloalkoxy" as used herein refers to a cycloalkyl radical, in particular a monocyclic cycloalkyl radical, as defined above having in particular 3 to 6 ("03-06-cycloalkoxy") or 3 to 5 ("03-05-cycloalkoxy") or 3 to 4 ("03-04-cycloalksoxy") carbon atoms, which is bound via an oxygen atom to the remainder of the molecule.
The term "cycloalkyl-C1-04-alkyl" refers to a 03-08-cycloalkyl ("03-08-cycloalkyl-C1-04-alkyl"), preferably a 03-06-cycloalkyl (03-06-cycloalkyl-01-04-alkyl), more preferably a 03-04-cycloalkyl ("03-04-cycloalkyl-C1-04-alkyl") as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a 01-04-alkyl group, as defined above. Examples for 03-04-cycloalkyl-C1-04-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutyl-methyl, cyclobutylethyl and cyclobutylpropyl, Examples for 03-06-cycloalkyl-01-04-alkyl, apart those mentioned for 03-04-cycloalkyl-C1-04-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpro-pyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
The term "01-02-alkoxy" is a 01-02-alkyl group, as defined above, attached via an oxygen atom. The term "01-03-alkoxy" is a 01-03-alkyl group, as defined above, attached via an oxygen atom.The term "01-04-alkoxy" is a 01-04-alkyl group, as defined above, attached via an oxygen atom. The term "01-06-alkoxy" is a 01-06-alkyl group, as defined above, attached via an oxygen atom. The term "01-010-alkoxy" is a 01-010-alkyl group, as defined above, attached via an oxygen atom. Ci-02-Alkoxy is OCH3 or 002H5. Ci-03-Alkoxy is additionally, for example, n-propoxy and 1-methylethoxy (isopropoxy). Ci-04-Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). Ci-06-Alkoxy is addition-ally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpent-oxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbut-oxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethy1-2-methylpropoxy. C1-08-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. C1-C10-Alkoxy is additionally, for example, nonyloxy, decyloxy and posi-tional isomers thereof.
The term "01-02-haloalkoxy" is a 01-02-haloalkyl group, as defined above, attached via an ox-ygen atom. The term "01-03-haloalkoxy" is a 01-03-haloalkyl group, as defined above, attached via an oxygen atom. The term "01-04-haloalkoxy" is a 01-04-haloalkyl group, as defined above, at-tached via an oxygen atom. The term "01-06-haloalkoxy" is a 01-06-haloalkyl group, as defined above, attached via an oxygen atom. 01-02-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, 00H201, 00H012, 00013, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroeth-oxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichlo-roethoxy or 002F5. 01-03-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 00H2-02F5, 00F2-02F5, 1-(CH2F)-2-fluoroethoxy, 1-(0H201)-2-chloroethoxy or 1-(0H2Br)-2-bromoethoxy. 01-04-
The term "cycloalkyl-C1-04-alkyl" refers to a 03-08-cycloalkyl ("03-08-cycloalkyl-C1-04-alkyl"), preferably a 03-06-cycloalkyl (03-06-cycloalkyl-01-04-alkyl), more preferably a 03-04-cycloalkyl ("03-04-cycloalkyl-C1-04-alkyl") as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a 01-04-alkyl group, as defined above. Examples for 03-04-cycloalkyl-C1-04-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutyl-methyl, cyclobutylethyl and cyclobutylpropyl, Examples for 03-06-cycloalkyl-01-04-alkyl, apart those mentioned for 03-04-cycloalkyl-C1-04-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpro-pyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
The term "01-02-alkoxy" is a 01-02-alkyl group, as defined above, attached via an oxygen atom. The term "01-03-alkoxy" is a 01-03-alkyl group, as defined above, attached via an oxygen atom.The term "01-04-alkoxy" is a 01-04-alkyl group, as defined above, attached via an oxygen atom. The term "01-06-alkoxy" is a 01-06-alkyl group, as defined above, attached via an oxygen atom. The term "01-010-alkoxy" is a 01-010-alkyl group, as defined above, attached via an oxygen atom. Ci-02-Alkoxy is OCH3 or 002H5. Ci-03-Alkoxy is additionally, for example, n-propoxy and 1-methylethoxy (isopropoxy). Ci-04-Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). Ci-06-Alkoxy is addition-ally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpent-oxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbut-oxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethy1-2-methylpropoxy. C1-08-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. C1-C10-Alkoxy is additionally, for example, nonyloxy, decyloxy and posi-tional isomers thereof.
The term "01-02-haloalkoxy" is a 01-02-haloalkyl group, as defined above, attached via an ox-ygen atom. The term "01-03-haloalkoxy" is a 01-03-haloalkyl group, as defined above, attached via an oxygen atom. The term "01-04-haloalkoxy" is a 01-04-haloalkyl group, as defined above, at-tached via an oxygen atom. The term "01-06-haloalkoxy" is a 01-06-haloalkyl group, as defined above, attached via an oxygen atom. 01-02-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, 00H201, 00H012, 00013, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroeth-oxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichlo-roethoxy or 002F5. 01-03-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 00H2-02F5, 00F2-02F5, 1-(CH2F)-2-fluoroethoxy, 1-(0H201)-2-chloroethoxy or 1-(0H2Br)-2-bromoethoxy. 01-04-
19 Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or no-nafluorobutoxy. 01-06-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromo-hexoxy, 6-iodohexoxy or dodecafluorohexoxy.
The term "01-06-alkoxy-01-04-alkyl" as used herein, refers to a straight-chain or branched al-kyl having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-06-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-meth-oxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxy-ethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobu-toxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxy-propyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypro-pyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl and the like.
The term "alkoxyalkoxy" as used herein refers to an alkoxyalkyl radical, in particular a 01-06-alkoxy-01-04-alkyl radical, as defined above, which is bound via an oxygen atom to the remainder of the molecule. Examples thereof are OCH2-0CH3, OCH2-002H5, n-propoxymethoxy, OCH2-0CH(CH3)2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-0C(CH3)3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methyleth-oxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-di-methylethoxy)ethoxy, etc.
The substituent "oxo" replaces a CH2 by a C(=0) group.
The term "aryl" relates to phenyl and bi- or polycyclic carbocycles having at least one fused phenylene ring, which is bound to the remainder of the molecule. Examples of bi- or polycyclic car-bocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl etc.
The term "aryl-CI-at-alkyl" relates to 01-04-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryl radical, in particular a phenyl radical.
Particular examples of aryl-Ci-04-alkyl include benzyl, 1-phenethyl, 2-phenetyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.
The term "aryloxy-C1-04-alkyl" relates to 01-04-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical.
Particular examples of aryloxy-C1-04-alkyl include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyetyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.
The term "aryl-CI-at-carbonyl" relates to aryl as defined aboveõ in particular a phenyl radi-cal, which is bound by a carbonyl to the remainder of the molecule. Particular examples of arylcar-bonyl include benzoyl, 1-naphthoyl and 2-naphthoyl.
The term hetaryl relates to aromatic heterocycles having either 5 or 6 ring atoms (5- or 6-membered hetaryl) and being monocyclic or 8, 9 or 10 ring atoms and bing bicyclic. Hetaryl will generally have at least one ring atom selected from 0, S and N, which in case of N may be an imino-nitrogen or an amino-nitrogen, which carries hydrogen or a radical different from hydrogen.
Hetaryl may have 1, 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens.
Examples of 5- or 6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyr-5 rolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-oxadiazolyI-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyri-dazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,3,5-triazin-2-yl..
Examples of 8-, 9- or 10-membered hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, 10 indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzimidazolyl, imidazo[1,2-a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl, imidazo42,1-b]-thiazol-6-y1 and 1,2,4-triazolo[1,5-a]pyridine-2-yl.
Examples of N-bound 5-, 6-, 7 or 8-membered saturated heterocycles include:
pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-15 yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-di-oxothiomorpholin-4-yl, azepan-1-y1 and the like.
The term "hetaryl-01-04-alkyl" relates to 01-04-alkyl, as defined above, wherein one hydrogen atom has been replaced by a hetaryl radical, in particular a pyridyl radical.
Particular examples of hetaryl-01-04-alkyl include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-
The term "01-06-alkoxy-01-04-alkyl" as used herein, refers to a straight-chain or branched al-kyl having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-06-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-meth-oxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxy-ethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobu-toxypropyl, 1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxy-propyl, 2-n-butoxypropyl, 2-sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypro-pyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl and the like.
The term "alkoxyalkoxy" as used herein refers to an alkoxyalkyl radical, in particular a 01-06-alkoxy-01-04-alkyl radical, as defined above, which is bound via an oxygen atom to the remainder of the molecule. Examples thereof are OCH2-0CH3, OCH2-002H5, n-propoxymethoxy, OCH2-0CH(CH3)2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-0C(CH3)3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methyleth-oxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-di-methylethoxy)ethoxy, etc.
The substituent "oxo" replaces a CH2 by a C(=0) group.
The term "aryl" relates to phenyl and bi- or polycyclic carbocycles having at least one fused phenylene ring, which is bound to the remainder of the molecule. Examples of bi- or polycyclic car-bocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, indanyl, indenyl, anthracenyl, fluorenyl etc.
The term "aryl-CI-at-alkyl" relates to 01-04-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryl radical, in particular a phenyl radical.
Particular examples of aryl-Ci-04-alkyl include benzyl, 1-phenethyl, 2-phenetyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1-propyl and 2-phenyl-2-propyl.
The term "aryloxy-C1-04-alkyl" relates to 01-04-alkyl, as defined above, wherein one hydrogen atom has been replaced by an aryloxy radical, in particular a phenoxy radical.
Particular examples of aryloxy-C1-04-alkyl include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyetyl, 1-phenoxypropyl, 2-phenoxypropyl, 3-phenoxy-1-propyl and 2-phenoxy-2-propyl.
The term "aryl-CI-at-carbonyl" relates to aryl as defined aboveõ in particular a phenyl radi-cal, which is bound by a carbonyl to the remainder of the molecule. Particular examples of arylcar-bonyl include benzoyl, 1-naphthoyl and 2-naphthoyl.
The term hetaryl relates to aromatic heterocycles having either 5 or 6 ring atoms (5- or 6-membered hetaryl) and being monocyclic or 8, 9 or 10 ring atoms and bing bicyclic. Hetaryl will generally have at least one ring atom selected from 0, S and N, which in case of N may be an imino-nitrogen or an amino-nitrogen, which carries hydrogen or a radical different from hydrogen.
Hetaryl may have 1, 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens.
Examples of 5- or 6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyr-5 rolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-oxadiazolyI-2-yl, 1,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyri-dazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,3,5-triazin-2-yl..
Examples of 8-, 9- or 10-membered hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, 10 indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzimidazolyl, imidazo[1,2-a]pyridine-2-yl, thieno[3,2-b]pyridine-5-yl, imidazo42,1-b]-thiazol-6-y1 and 1,2,4-triazolo[1,5-a]pyridine-2-yl.
Examples of N-bound 5-, 6-, 7 or 8-membered saturated heterocycles include:
pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, isoxazolidin-2-yl, thiazolidin-3-yl, isothiazolidin-2-15 yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-4-yl, 1,1-di-oxothiomorpholin-4-yl, azepan-1-y1 and the like.
The term "hetaryl-01-04-alkyl" relates to 01-04-alkyl, as defined above, wherein one hydrogen atom has been replaced by a hetaryl radical, in particular a pyridyl radical.
Particular examples of hetaryl-01-04-alkyl include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1-(2-pyridyl)ethyl, 2-(2-
20 pyridyl)ethyl, 1-(3-pyridyl)ethyl, 2-(3-pyridyl)ethyl, 1-(4-pyridyl)ethyl, 2-(4-pyridyl)ethyl etc..
The term "hetaryloxy-01-04-alkyl" relates to 01-04-alkyl, as defined above, wherein one hy-drogen atom has been replaced by an hetaryloxy radical, in particular a pyridyloxy radical. Particu-lar examples of hetaryloxy-01-04-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyri-dyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3-pyri-dyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl etc.
The term "hetaryl-01-04-carbonyl" relates to hetaryl as defined above, in particular a C-bound hetaryl radical, e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrim-idinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazoly1 radical, which is bound by a carbonyl to the remainder of the molecule.
The term "substituted" if not specified otherwise refers to substituted with 1, 2 or maximum possi-ble number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.
With respect to the variables, the embodiments of the compounds of the formula I are, In one embodiment, A is CRA
In another embodiment, A is N.
In one embodiment, G is CRB.
In another embodiment, G is N.
In one embodiment, A is CRA and G is N.
In another embodiment, A is N and G is CRB.
In another embodiment, A is N and G is N.
The term "hetaryloxy-01-04-alkyl" relates to 01-04-alkyl, as defined above, wherein one hy-drogen atom has been replaced by an hetaryloxy radical, in particular a pyridyloxy radical. Particu-lar examples of hetaryloxy-01-04-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyri-dyloxymethyl, 1-(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1-(3-pyridyloxy)ethyl, 2-(3-pyri-dyloxy)ethyl, 1-(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl etc.
The term "hetaryl-01-04-carbonyl" relates to hetaryl as defined above, in particular a C-bound hetaryl radical, e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrim-idinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazoly1 radical, which is bound by a carbonyl to the remainder of the molecule.
The term "substituted" if not specified otherwise refers to substituted with 1, 2 or maximum possi-ble number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.
With respect to the variables, the embodiments of the compounds of the formula I are, In one embodiment, A is CRA
In another embodiment, A is N.
In one embodiment, G is CRB.
In another embodiment, G is N.
In one embodiment, A is CRA and G is N.
In another embodiment, A is N and G is CRB.
In another embodiment, A is N and G is N.
21 In another embodiment, A is CRA and G is ORB.
In one embodiment, R is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In more preferred embodiment, R is H, halogen, OH, ON, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In most preferred embodiment, R is H, CI, Br, F, OH, ON, CH3, 02H5, n-03H7, isopropyl, cyclopro-pyl, allyl and propargyl, CH2F, CHF2, CF3, 00H3, 002H5, OCH2F, OCHF2, 00F3, 00H20H20F3, OCH2CF2CH F2, or 00H20F20F3.
In one embodiment, RA is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In more preferred embodiment, RA is H, halogen, OH, ON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In most preferred embodiment, RA is H, CI, Br, F, OH, ON, CH3, 02H5, n-03H7, isopropyl, cyclopro-pyl, allyl and propargyl, CH2F, CHF2, CF3, 00H3, 002H5, OCH2F, OCHF2, 00F3, 00H20H20F3, OCH2CF2CHF2, or 00H20F20F3.
In one embodiment, RB is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In more preferred embodiment, RB is H, halogen, OH, ON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In most preferred embodiment, RB is H, CI, Br, F, OH, ON, CH3, 02H5, n-03H7, isopropyl, cyclopro-pyl, allyl and propargyl, CH2F, CHF2, CF3, 00H3, 002H5, OCH2F, OCHF2, 00F3, 00H20H20F3, OCH2CF2CHF2, or 00H20F20F3.
In one embodiment, Q is NR2.
In another embodiment, Q is 0.
In another embodiment, Q is S.
In another embodiment, Q is S(=0).
In another embodiment, Q is S(=0)2.
In more preferred embodiment compounds of formula I are selected from compounds of formula IA to IT wherein R1, RA, RB, R2 and Ar are as defined herein.
RAR1 RAyR1 Ar,NNRB Ar,NN.RB N Ar,N1\r N
,12 12 30 12 ,1 2 rµ R 1.13 R I.0 I.D
A
Ar,0RB Ar,0)NjRB Ar, N Ar, N
0 N' 0 N' I.E I.F I.G I.H
In one embodiment, R is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In more preferred embodiment, R is H, halogen, OH, ON, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In most preferred embodiment, R is H, CI, Br, F, OH, ON, CH3, 02H5, n-03H7, isopropyl, cyclopro-pyl, allyl and propargyl, CH2F, CHF2, CF3, 00H3, 002H5, OCH2F, OCHF2, 00F3, 00H20H20F3, OCH2CF2CH F2, or 00H20F20F3.
In one embodiment, RA is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In more preferred embodiment, RA is H, halogen, OH, ON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In most preferred embodiment, RA is H, CI, Br, F, OH, ON, CH3, 02H5, n-03H7, isopropyl, cyclopro-pyl, allyl and propargyl, CH2F, CHF2, CF3, 00H3, 002H5, OCH2F, OCHF2, 00F3, 00H20H20F3, OCH2CF2CHF2, or 00H20F20F3.
In one embodiment, RB is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In more preferred embodiment, RB is H, halogen, OH, ON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, or tri-01-06-alkylsilyl.
In most preferred embodiment, RB is H, CI, Br, F, OH, ON, CH3, 02H5, n-03H7, isopropyl, cyclopro-pyl, allyl and propargyl, CH2F, CHF2, CF3, 00H3, 002H5, OCH2F, OCHF2, 00F3, 00H20H20F3, OCH2CF2CHF2, or 00H20F20F3.
In one embodiment, Q is NR2.
In another embodiment, Q is 0.
In another embodiment, Q is S.
In another embodiment, Q is S(=0).
In another embodiment, Q is S(=0)2.
In more preferred embodiment compounds of formula I are selected from compounds of formula IA to IT wherein R1, RA, RB, R2 and Ar are as defined herein.
RAR1 RAyR1 Ar,NNRB Ar,NN.RB N Ar,N1\r N
,12 12 30 12 ,1 2 rµ R 1.13 R I.0 I.D
A
Ar,0RB Ar,0)NjRB Ar, N Ar, N
0 N' 0 N' I.E I.F I.G I.H
22 R R R R
A
/ Nr j Ar,Sõ,....-N.õ.....õ..RB Ar.1õ,.....N...õ--...,RB Ar, N Al-, N
S N' S N' 1.1 I.J I.K I.L
R R R R
/ / N .
I J
Ar,S_...--s..Nõ...-B Ar,S.,..k.Nõ....--.,RB Ar, N Ar, N
S Nr S 1\l' 8 i.m \\
1.0 I.N 0 0 I.P
R R R R
RA N
R1 r / / j Ar,ii B Ar 11,.....- N R r, B Aii N At-, ) IN
S
8 I.Q \\ o I.R // IS ll I.T
wherein, Ar is phenyl or 5- or 6-membered hetaryl ring which is substituted with RAr;
RAr is halogen, OH, ON, NO2, SON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or S-Re, which are unsubstituted or substituted with halogen;
R2 is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, or 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, and phenyl which is unsubstituted or substituted with Rf;
R is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyl;
RA is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyl;
RB is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyl;
and R1 is X-Y-Z-T-R11 and X-Y-Z-T-R12, as defined in formula I.
In another more preferred embodiment compounds of formula I are selected from compounds of formula I.A.1, I.A.2, I.A.3, 1.6.1, 1.6.2, 1.6.3, 1.6.4, 1.6.5, IØ1, IØ1, IØ2, I.D.1, I.D.2, I.E.1, I.E.2, I.E.3, I.E.4, I.F.1, I.F.2, I.F.3, I.F.4, 1.F.5, I.G.1, I.G.2, I.G.1, I.H.1, I.H.2, 1.1.1, 1.1.2, 1.1.3, I.J.1, I.J.2, I.J.3, I.J.4, I.J.5, I.K.1, I.K.2, I.K.3, I.L.1, I.L.2, I.M.1, I.M.2, I.M.3, I.N.1, I.N.2, I.N.3, I.N.4, 1Ø1, 1Ø2, 1Ø3, I.P.1, I.P.2, I.Q.1, I.Q.2, I.Q.3, I.R.1, I.R.2, I.R.3, I.R.4, I.S.1, I.S.2, I.S.3, I.T.1, I.T.2, and I.T.3, wherein R1, R2, and Ar are as defined herein.
,R1 N\ N\
Ar Ar XIR I I
Ar Ar, Aro:
C H3 i\l 1\1- N N
R
I.A.1 I.A.2 I.A.3 1.6.1 1.6.2
A
/ Nr j Ar,Sõ,....-N.õ.....õ..RB Ar.1õ,.....N...õ--...,RB Ar, N Al-, N
S N' S N' 1.1 I.J I.K I.L
R R R R
/ / N .
I J
Ar,S_...--s..Nõ...-B Ar,S.,..k.Nõ....--.,RB Ar, N Ar, N
S Nr S 1\l' 8 i.m \\
1.0 I.N 0 0 I.P
R R R R
RA N
R1 r / / j Ar,ii B Ar 11,.....- N R r, B Aii N At-, ) IN
S
8 I.Q \\ o I.R // IS ll I.T
wherein, Ar is phenyl or 5- or 6-membered hetaryl ring which is substituted with RAr;
RAr is halogen, OH, ON, NO2, SON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or S-Re, which are unsubstituted or substituted with halogen;
R2 is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, or 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, and phenyl which is unsubstituted or substituted with Rf;
R is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyl;
RA is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyl;
RB is H, halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or 02-06-alkenyl;
and R1 is X-Y-Z-T-R11 and X-Y-Z-T-R12, as defined in formula I.
In another more preferred embodiment compounds of formula I are selected from compounds of formula I.A.1, I.A.2, I.A.3, 1.6.1, 1.6.2, 1.6.3, 1.6.4, 1.6.5, IØ1, IØ1, IØ2, I.D.1, I.D.2, I.E.1, I.E.2, I.E.3, I.E.4, I.F.1, I.F.2, I.F.3, I.F.4, 1.F.5, I.G.1, I.G.2, I.G.1, I.H.1, I.H.2, 1.1.1, 1.1.2, 1.1.3, I.J.1, I.J.2, I.J.3, I.J.4, I.J.5, I.K.1, I.K.2, I.K.3, I.L.1, I.L.2, I.M.1, I.M.2, I.M.3, I.N.1, I.N.2, I.N.3, I.N.4, 1Ø1, 1Ø2, 1Ø3, I.P.1, I.P.2, I.Q.1, I.Q.2, I.Q.3, I.R.1, I.R.2, I.R.3, I.R.4, I.S.1, I.S.2, I.S.3, I.T.1, I.T.2, and I.T.3, wherein R1, R2, and Ar are as defined herein.
,R1 N\ N\
Ar Ar XIR I I
Ar Ar, Aro:
C H3 i\l 1\1- N N
R
I.A.1 I.A.2 I.A.3 1.6.1 1.6.2
23 N-'R
N- NJX n7 Ar,NNj-C H3 Ark N,i I
Ar \1 1\1 CI , 1\1 CI ArNWN ArN
R R R R R
1.6.3 1.6.4 1.6.5 IØ1 IØ1 Nnr NjyR1 R1 1 Ar,'N I
Ar'1\1N1'N N N Ar,N)N'N I
12 Ar,0Nj Ar,0NCH 3 R R
IØ2 I.D.1 I.D.2 I.E.1 I.E.2 N
R Nj N R
Ar 1 Ar Ar,oN Ar 'ONCH3 'IONCH3 C H3 Ar'elN1C H3 I.E.3 I.E.4 I.F.1 I.F.2 I.F.3 R
N/ N JYR
nR H
Ar, k Ar Ar N Ar, N Ar, N
I.F.4 I.F.5 I.G.1 I.G.2 I.G.1 NJ
r1 Nnr I I
Ar,SN Ar, Ar, Ar, N Ar, N
0 N' 0 N' S N CH3 S N CH3 I.H.1 I.H.2 1.1.1 1.1.2 1.1.3 1 Ri Ny R Ni . s Nj R
Ar,SNj Ar, Ar, I
SNCH3 Ar SNCH3 ,SN 01 CI
N
Ar, k S N CI
I.J.1 I.J.2 I.J.3 I.J.4 I.J.5 N
R H3C.....,õcõ./.....r.õR
nR
JY I Nr r Ar, N At-, N Ar, N Ar, N At-, N
S N' S
N' I.K.1 I.K.2 I.K.3 I.L.1 I.L.2
N- NJX n7 Ar,NNj-C H3 Ark N,i I
Ar \1 1\1 CI , 1\1 CI ArNWN ArN
R R R R R
1.6.3 1.6.4 1.6.5 IØ1 IØ1 Nnr NjyR1 R1 1 Ar,'N I
Ar'1\1N1'N N N Ar,N)N'N I
12 Ar,0Nj Ar,0NCH 3 R R
IØ2 I.D.1 I.D.2 I.E.1 I.E.2 N
R Nj N R
Ar 1 Ar Ar,oN Ar 'ONCH3 'IONCH3 C H3 Ar'elN1C H3 I.E.3 I.E.4 I.F.1 I.F.2 I.F.3 R
N/ N JYR
nR H
Ar, k Ar Ar N Ar, N Ar, N
I.F.4 I.F.5 I.G.1 I.G.2 I.G.1 NJ
r1 Nnr I I
Ar,SN Ar, Ar, Ar, N Ar, N
0 N' 0 N' S N CH3 S N CH3 I.H.1 I.H.2 1.1.1 1.1.2 1.1.3 1 Ri Ny R Ni . s Nj R
Ar,SNj Ar, Ar, I
SNCH3 Ar SNCH3 ,SN 01 CI
N
Ar, k S N CI
I.J.1 I.J.2 I.J.3 I.J.4 I.J.5 N
R H3C.....,õcõ./.....r.õR
nR
JY I Nr r Ar, N At-, N Ar, N Ar, N At-, N
S N' S
N' I.K.1 I.K.2 I.K.3 I.L.1 I.L.2
24 R N N
Ai-, 1 Ar,SNC H3 S Ar 'S..-NCH S N
i.m.i I.M.2 I.M.3 I.N.1 I.N.2 N / R Nj/
Ar, S Ai-, j= Ar- õ N A Ar- N N CH3 S N
CI S¨N' l'S/N'INI
S N' 0 // II ii II
I.N.3 I.N.4 1Ø1 1Ø2 1Ø3 Ny N
R
ALS
N Ar, N Ar, ii j Ar, II Ar-,g,N jC
N' S N' S N N CH3 Il II
I.P.1 I.P.2 1Ø1 1Ø2 1Ø3 Ri ON )Ri Ri I 0 NIRi Or 0 N 1 0 Ar_g_ Ar _g4 Ar¨ g...N 1CH3 Ar I¨ g...Nj=CI
Ar-.NN
II N ii N CH3 II II
I.R.1 I.R.2 I.R.3 I.R.4 I.S.1 R1 ) 0 Ny R1 . 0 N 1 0 1 I Or 1 Ar ii, N Ar N
, II N Ar-IN,N Ar,V N,1\1 -S N' S ' N CI
O 8 ii I.S.2 I.S.3 I.T.1 I.T.2 I.T.3 In one embodiment, R2 is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, which are unsubstituted or substituted with R.
In more preferred embodiment, R2 is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, or 03-06-cycloalkyl.
In most preferred embodiment, R2 is H, CH3, 02H5, n-03H7, isopropyl, cyclopropyl, allyl and pro-pargyl, CH2F, CH F2, C F3, CH2F, CH F2, CF3, or phenyl which is unsubstituted or substituted with R.
In one embodiment, Ar is phenyl which is unsubstituted or substituted with RAr.
In another embodiment, Ar is 5- or 6-membered hetaryl, which is unsubstituted or substituted with RAr.
In another embodiment, Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridyl, which are unsubstituted substituted with R.
In one embodiment, RAr is halogen, OH, ON, NO2, SON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or S-Re, which are unsubstituted substituted with halogen.
In more preferred embodiment, RAr is F, CI , Br, OH, ON, NO2, SON, CH3, 02H5, n-03H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, 02F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, 002H5, 5 n-propyloxy, isopropyloxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, 002F5, OCH2CH2CF3, OCH2CF2CH F2, OCH2CF2CF3, or S-Re, where Re is 01-06-alkyl, in particular 01-03-alkyl such asCH3, 02H5, n-03H7 or isopropyl, or 01-06-haloalkyl, in particular fluorinated 01-03-alkyl such as CH2F, CHF2, CF3, 0H20F3, CF2CHF2, 02F5, 0H20H20F3, CH2CF2CHF2or CH2CF2CF3.
Preferred Ar are the radicals Ar-1 to Ar-12 summarized in Table A below.
10 Table A: Examples of radicals Ar Ar-1 Ar-5 N F N=N
Ar-9 F3C Fe Ar-Ar-2 4)\ N 0 Ar-6 F3 10 F3C,01 Ar-3 4)\ Ar-F5C2 I Ar-7 11 CF3 .,o C2 Ar-4 Ar- F3Cr F3C'sI Ar-8 N S
N-N
In one embodiment, R1 is X-Y-Z-T-R11.
In another embodiment, R1 is X-Y-Z-T-R12.
In one embodiment, X is -CRxaRxb-.
15 In another embodiment, X is -0-.
In another embodiment, X is -S-.
In another embodiment, X is -NRxc-.
In another embodiment, X is -CRxa=CRxb-.
In another embodiment, X is -CRxaRxb-CRxaRxb-.
20 In another embodiment, X is -0-CRxaRxb-.
In another embodiment, X is -S-CRxaRxb-.
In another embodiment, X is In another embodiment, X is -NRxc-CRxaRxb-, wherein CRxaRxb is bound to Y.
In another embodiment, X is -NRxb-C(=S)-.
Ai-, 1 Ar,SNC H3 S Ar 'S..-NCH S N
i.m.i I.M.2 I.M.3 I.N.1 I.N.2 N / R Nj/
Ar, S Ai-, j= Ar- õ N A Ar- N N CH3 S N
CI S¨N' l'S/N'INI
S N' 0 // II ii II
I.N.3 I.N.4 1Ø1 1Ø2 1Ø3 Ny N
R
ALS
N Ar, N Ar, ii j Ar, II Ar-,g,N jC
N' S N' S N N CH3 Il II
I.P.1 I.P.2 1Ø1 1Ø2 1Ø3 Ri ON )Ri Ri I 0 NIRi Or 0 N 1 0 Ar_g_ Ar _g4 Ar¨ g...N 1CH3 Ar I¨ g...Nj=CI
Ar-.NN
II N ii N CH3 II II
I.R.1 I.R.2 I.R.3 I.R.4 I.S.1 R1 ) 0 Ny R1 . 0 N 1 0 1 I Or 1 Ar ii, N Ar N
, II N Ar-IN,N Ar,V N,1\1 -S N' S ' N CI
O 8 ii I.S.2 I.S.3 I.T.1 I.T.2 I.T.3 In one embodiment, R2 is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, which are unsubstituted or substituted with R.
In more preferred embodiment, R2 is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, or 03-06-cycloalkyl.
In most preferred embodiment, R2 is H, CH3, 02H5, n-03H7, isopropyl, cyclopropyl, allyl and pro-pargyl, CH2F, CH F2, C F3, CH2F, CH F2, CF3, or phenyl which is unsubstituted or substituted with R.
In one embodiment, Ar is phenyl which is unsubstituted or substituted with RAr.
In another embodiment, Ar is 5- or 6-membered hetaryl, which is unsubstituted or substituted with RAr.
In another embodiment, Ar is phenyl, pyrimidinyl, pyridazinyl, or pyridyl, which are unsubstituted substituted with R.
In one embodiment, RAr is halogen, OH, ON, NO2, SON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, or S-Re, which are unsubstituted substituted with halogen.
In more preferred embodiment, RAr is F, CI , Br, OH, ON, NO2, SON, CH3, 02H5, n-03H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, 02F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, 002H5, 5 n-propyloxy, isopropyloxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, 002F5, OCH2CH2CF3, OCH2CF2CH F2, OCH2CF2CF3, or S-Re, where Re is 01-06-alkyl, in particular 01-03-alkyl such asCH3, 02H5, n-03H7 or isopropyl, or 01-06-haloalkyl, in particular fluorinated 01-03-alkyl such as CH2F, CHF2, CF3, 0H20F3, CF2CHF2, 02F5, 0H20H20F3, CH2CF2CHF2or CH2CF2CF3.
Preferred Ar are the radicals Ar-1 to Ar-12 summarized in Table A below.
10 Table A: Examples of radicals Ar Ar-1 Ar-5 N F N=N
Ar-9 F3C Fe Ar-Ar-2 4)\ N 0 Ar-6 F3 10 F3C,01 Ar-3 4)\ Ar-F5C2 I Ar-7 11 CF3 .,o C2 Ar-4 Ar- F3Cr F3C'sI Ar-8 N S
N-N
In one embodiment, R1 is X-Y-Z-T-R11.
In another embodiment, R1 is X-Y-Z-T-R12.
In one embodiment, X is -CRxaRxb-.
15 In another embodiment, X is -0-.
In another embodiment, X is -S-.
In another embodiment, X is -NRxc-.
In another embodiment, X is -CRxa=CRxb-.
In another embodiment, X is -CRxaRxb-CRxaRxb-.
20 In another embodiment, X is -0-CRxaRxb-.
In another embodiment, X is -S-CRxaRxb-.
In another embodiment, X is In another embodiment, X is -NRxc-CRxaRxb-, wherein CRxaRxb is bound to Y.
In another embodiment, X is -NRxb-C(=S)-.
25 In another embodiment, X is -N=C(S-Re)-.
In another embodiment, X is -NRxb-C(=0)-.
In one embodiment, Y is -CRYa=N-, wherein the N is bound to Z.
In another embodiment, Y is -NRYb-C(=S)-, wherein C(=S) is bound to Z.
In another embodiment, Y is -NRYb-C(=0)-, wherein C(=0) is bound to Z.
In another embodiment, X is -NRxb-C(=0)-.
In one embodiment, Y is -CRYa=N-, wherein the N is bound to Z.
In another embodiment, Y is -NRYb-C(=S)-, wherein C(=S) is bound to Z.
In another embodiment, Y is -NRYb-C(=0)-, wherein C(=0) is bound to Z.
26 In one embodiment, Z is -NRzc-C(=S)-, wherein C(=S) is bound to T.
In another embodiment, Z is -NRzc-C(=0)-, wherein C(=0) is bound to T.
In another embodiment, Z is-N=C(S-Rza)-, wherein T is bound to the carbon atom.
In another embodiment, Z is -0-C(=0)-, wherein T is bound to the carbon atom.
In another embodiment, Z is -0-C(=S)-, wherein T is bound to the carbon atom.
In another embodiment, Z is-NRzc-C(S-Rza)=, wherein T is bound to the carbon atom.
In another embodiment, Z is a single bond.
In one embodiment, T is 0.
In another embodiment, T is N-RT.
In another embodiment, T is N.
In one embodiment, Rxa, Rxb, RYa are H, halogen, 01-06-alkyl, 01-06-alkoxy, 01-06-haloalkyl, 06-haloalkoxy, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Rxa, Rxb, RYa are H, halogen, 01-06-alkyl, 01-06-alkoxy, which are unsubstituted or substituted with halogen, , or phenyl which is unsubstituted or substituted with R.
In most preferred embodiment, Rxa, Rxb, Rya are H, F, Cl, Br, CH3, 02H5, n-03H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, 02F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, 002H5, n-propyloxy, isopropyloxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, 002F5, OCH2CH2CF3, OCH2CF2CH F2, OCH2CF2CF3, or phenyl which is unsubstituted or substituted with R.
In one embodiment, Rxc, RYc, Rzc are H, 01-06-alkyl, 01-06-haloalkyl, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Rxc, RYc, Rzc are H, 01-06-alkyl, which are unsubstituted or substi-tuted with halogen, or phenyl which is unsubstituted or substituted with R.
In most preferred embodiment, Rxc, RYc, Rzc are H, CH3, 02H5, n-03H7, isopropyl, CH2F, CHF2, CF3, 0H20F3, CF2CHF2, 02F5, 0H20H20F3, CH2CF2CH F2, 0H20F20F3, or phenyl which is unsubstituted or substituted with R.
In one embodiment, RT is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, which are unsubstituted or substituted with halogen, C(0)-NRhRc, C(0)-Rd, SO2NRhRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In another embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be replaced by a carbonyl or a O=N-R and/or wherein 1 or 2 CH2 moieties may be replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubsti-tuted or substituted with Rh.
In more preferred embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a carbonyl group.
In another embodiment, Z is -NRzc-C(=0)-, wherein C(=0) is bound to T.
In another embodiment, Z is-N=C(S-Rza)-, wherein T is bound to the carbon atom.
In another embodiment, Z is -0-C(=0)-, wherein T is bound to the carbon atom.
In another embodiment, Z is -0-C(=S)-, wherein T is bound to the carbon atom.
In another embodiment, Z is-NRzc-C(S-Rza)=, wherein T is bound to the carbon atom.
In another embodiment, Z is a single bond.
In one embodiment, T is 0.
In another embodiment, T is N-RT.
In another embodiment, T is N.
In one embodiment, Rxa, Rxb, RYa are H, halogen, 01-06-alkyl, 01-06-alkoxy, 01-06-haloalkyl, 06-haloalkoxy, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Rxa, Rxb, RYa are H, halogen, 01-06-alkyl, 01-06-alkoxy, which are unsubstituted or substituted with halogen, , or phenyl which is unsubstituted or substituted with R.
In most preferred embodiment, Rxa, Rxb, Rya are H, F, Cl, Br, CH3, 02H5, n-03H7, isopropyl, CH2F, CHF2, CF3, CH2CF3, CF2CHF2, 02F5, CH2CH2CF3, CH2CF2CHF2, CH2CF2CF3, OCH3, 002H5, n-propyloxy, isopropyloxy, OCH2F, OCHF2, OCF3, OCH2CF3, OCF2CHF2, 002F5, OCH2CH2CF3, OCH2CF2CH F2, OCH2CF2CF3, or phenyl which is unsubstituted or substituted with R.
In one embodiment, Rxc, RYc, Rzc are H, 01-06-alkyl, 01-06-haloalkyl, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Rxc, RYc, Rzc are H, 01-06-alkyl, which are unsubstituted or substi-tuted with halogen, or phenyl which is unsubstituted or substituted with R.
In most preferred embodiment, Rxc, RYc, Rzc are H, CH3, 02H5, n-03H7, isopropyl, CH2F, CHF2, CF3, 0H20F3, CF2CHF2, 02F5, 0H20H20F3, CH2CF2CH F2, 0H20F20F3, or phenyl which is unsubstituted or substituted with R.
In one embodiment, RT is H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-04-alkyl-01-06-alkoxy, which are unsubstituted or substituted with halogen, C(0)-NRhRc, C(0)-Rd, SO2NRhRc, S(=0)mRe, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In another embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be replaced by a carbonyl or a O=N-R and/or wherein 1 or 2 CH2 moieties may be replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubsti-tuted or substituted with Rh.
In more preferred embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a carbonyl group.
27 In another more preferred embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a C=N-R and wherein 1 or 2 CH2 moieties may be replaced by 0 or S
and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In another more preferred embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene 1 or 2 CH2 moieties are replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In one embodiment, Rza is H, 01-06-haloalkyl, Ci-C6-alkylen-NRbRc, 01-06-C(0)-Rd, phenyl, phenylcarbonyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In another embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be replaced by a carbonyl or a O=N-R' and/or wherein 1 or 2 CH2 moieties may be replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubsti-tuted or substituted with Rh.
In more preferred embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a carbonyl group.
In another more preferred embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a O=N-R' and wherein 1 or 2 CH2 moieties may be replaced by 0 or S
and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In another more preferred embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene 1 or 2 CH2 moieties are replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In a preferred embodiment, Ra, Rb and Rc are H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, which are unsubstituted or substituted with halogen, 01-06-alkylen-ON, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
In more preferred embodiment, Ra, Rb and Rc are H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In a preferred embodiment, Rd is H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Rd is H, 01-06-haloalkyl, or phenyl which is unsubsti-tuted or substituted with R.
In one embodiment, Reis 01-06-alkyl, 01-06-haloalkyl, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen,
and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In another more preferred embodiment, Rzc together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene 1 or 2 CH2 moieties are replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In one embodiment, Rza is H, 01-06-haloalkyl, Ci-C6-alkylen-NRbRc, 01-06-C(0)-Rd, phenyl, phenylcarbonyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In another embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety may be replaced by a carbonyl or a O=N-R' and/or wherein 1 or 2 CH2 moieties may be replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubsti-tuted or substituted with Rh.
In more preferred embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a carbonyl group.
In another more preferred embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene a CH2 moiety is replaced by a O=N-R' and wherein 1 or 2 CH2 moieties may be replaced by 0 or S
and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In another more preferred embodiment, Rza together with RT if present, forms 01-06-alkylene or a linear 02-06-alkenylene group, where in the linear 01-06-alkylene and the linear 02-06-alkenylene 1 or 2 CH2 moieties are replaced by 0 or S and/or wherein the linear 01-06-alkylene and the linear 02-06-alkenylene may be unsubstituted or substituted with Rh.
In a preferred embodiment, Ra, Rb and Rc are H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, which are unsubstituted or substituted with halogen, 01-06-alkylen-ON, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
In more preferred embodiment, Ra, Rb and Rc are H, 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In a preferred embodiment, Rd is H, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Rd is H, 01-06-haloalkyl, or phenyl which is unsubsti-tuted or substituted with R.
In one embodiment, Reis 01-06-alkyl, 01-06-haloalkyl, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen,
28 phenyl, or benzyl, wherein the rings are unsubstituted or substituted with R.
In more preferred embodiment, Re is H, 01-06-alkyl, 01-06-haloalkyl, or phenyl which is unsubsti-tuted or substituted with R.
In one embodiment, Rf is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-C6-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, 03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, 01-06-alkylen-ON, C(0)-NRbRc, C(0)-Rd, 5O2NRbRc, or S(=0)mRe.
In more preferred embodiment, Rf is halogen, N3, OH, ON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, 03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, 01-06-alkylen-ON, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe.
In a preferred embodiment, Rg is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, 03-06-cy-cloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylell-NRbRc, NH-Ci-C6-alkylell-NRbRc, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe.
In more preferred embodiment, Rg is halogen, N3, OH, ON, NO2, 01-06-alkyl, 01-06-haloalkyl, Oi-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 03-06-cycloalkyl, 03-06-cycloalkoxy, which are unsub-stituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe.
In one embodiment, m is 0.
In another embodiment, m is 1.
In another embodiment, m is 2.
Particularly preferred X-Y-Z-T are formulas XYZT-1 to XYZT-19 wherein denotes attachment to the 6 membered hetaryl and # denotes attachment to R11 or R12, and wherein Re, xa, xb, xy and xc are as defined in compounds of formula I.
Rxa Rxa Rya 1# Rxa Rxb Rya N yN
xbNr Rxb Rxa R s RYa Rya Rxc RYa N- -Lyo Rxa Rxb Rxa Rxa Rxb
In more preferred embodiment, Re is H, 01-06-alkyl, 01-06-haloalkyl, or phenyl which is unsubsti-tuted or substituted with R.
In one embodiment, Rf is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-C6-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, 03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, 01-06-alkylen-ON, C(0)-NRbRc, C(0)-Rd, 5O2NRbRc, or S(=0)mRe.
In more preferred embodiment, Rf is halogen, N3, OH, ON, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, 03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, 01-06-alkylen-ON, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe.
In a preferred embodiment, Rg is halogen, N3, OH, ON, NO2, -SON, -SF5, 01-06-alkyl, 01-06-haloalkyl, 01-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, 03-06-cy-cloalkoxy, which are unsubstituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylell-NRbRc, NH-Ci-C6-alkylell-NRbRc, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe.
In more preferred embodiment, Rg is halogen, N3, OH, ON, NO2, 01-06-alkyl, 01-06-haloalkyl, Oi-06-alkoxy, 01-06-haloalkoxy, 02-06-alkenyl, 03-06-cycloalkyl, 03-06-cycloalkoxy, which are unsub-stituted or substituted with halogen, C(0)-0Ra, NRbRc, Ci-C6-alkylen-NRbRc, C(0)-NRbRc, C(0)-Rd, SO2NRbRc, or S(=0)mRe.
In one embodiment, m is 0.
In another embodiment, m is 1.
In another embodiment, m is 2.
Particularly preferred X-Y-Z-T are formulas XYZT-1 to XYZT-19 wherein denotes attachment to the 6 membered hetaryl and # denotes attachment to R11 or R12, and wherein Re, xa, xb, xy and xc are as defined in compounds of formula I.
Rxa Rxa Rya 1# Rxa Rxb Rya N yN
xbNr Rxb Rxa R s RYa Rya Rxc RYa N- -Lyo Rxa Rxb Rxa Rxa Rxb
29 Rxc RYa # Rya # Rxc RP #
riy N N N, NN 0 N N N
_t0 N 1._.t0 y - -1- \N yL l S S S
'Re S 0 S
Rxa RYc # Rxa RYao--\s Rxa RYc \.11 N N VYLNI'N vy 0, Rxb 0 s N¨# Rxb 0 0 Rxa RYc xa Yc RYc #
R R 1#
I I i I\L /N¨# 0y N T Ny N N
_NI
VYLNr y o Rxb 0 Rxb 0 Rxa 0 S
RYc T #
\
Rxa RYc INiy RN RYa H
N / .yL 0 # N' y # \o NI 1-1 ' y NI,I.R' T
0 S Rxa Rxb S
Rxb Rxa Rxb Rya #
\XL Nj N' ,RT
,Rxa,\Rxb sy lo XYZT-19 Also particularly preferred X-Y-Z-T are formulas XYZT-1 to XYZT-16;
Also particularly preferred X-Y-Z-T are formulas XYZT-17 to XYZT-19;
In one embodiment, R11 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, aryl, arylcarbonyl, aryl-CI-at-alkyl, aryloxy-C1-04-alkyl, hetaryl, carbonylhetaryl, 01-04-alkyl-hetaryl and 01-04-alkyl-hetaryloxy, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl.
In more preferred embodiment, R11 01-06-alkyl, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, aryl, arylcarbonyl, aryl-CI-at-alkyl, aryloxy-C1-04-alkyl, hetaryl, carbonylhetaryl, 01-04-alkyl-hetaryl and 01-04-alkyl-hetaryloxy, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl.
In most preferred embodiment, R11 aryl, aryl-CI-at-alkyl, hetaryl, or hetaryl-01-04-alkyl, wherein the rings are unsubstituted or substituted with Rg and where hetaryl in hetaryl or hetaryl-01-04-alkyl, is preferably a 5- or 6-membered monocyclic hetaryl such as pyridyl, pyrimidinyl, pyridazinyl, pyr-rolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl which is unsubstituted or substituted with Rg.
Examples of particularly preferred radicals R11 are the radicals R11-1 to R11-29 summarized in Ta-5 ble B below.
Table B: Examples of radicals R11 R11-1 R11-11 F F ________________________ -CH el R11_20 N
!
H3C'O
C
R11-2 R11_12 I CI R11_21 lel Or ;ICI
F
I
F
F CI
)1,1 a CI CH3 R11-23 el I
ci ocH3 I
H3C. R11-24 a\
F
CI CI
F
R11-6 =A, R11_16 F R11_25 \`1, I I
F
H3CCH3-'CH3 el CI R11-17 H3C 0 Br R11_26 F F
lei Cl R11_27 H3C 0 CH3 !NJ:c H3 R11-28 I I
F
I. F R11_19 !NCH3 jrc.._õ,......H3 .,...."
C.
R11_10 H3 F
e IA
- .3 In one embodiment, R12 is a radical of the formula (A1), (A1) wherein # indicates the point of attachment to T and wherein R121, R122, R123and R124 are as de-fined above and wherein R121, R122, R123and R124 independently of each other and especially in combination preferably have the following meanings:
Ri2i is 01204_ alkoxy, in particular OCH3, 002H5;
R122 is 01-04-alkoxy, such as OCH3, 002H5, n-propoxyx or isopropoxy, or 03-04-alkenyloxy, such as allyloxy, with R122 in particular being OCH3, 002H5, or n-propoxy;
R123 is OH, 01-04-alkoxy, such as OCH3, 002H5õ or 03-04-alkenyloxy, such as allyloxy, with R123 in particular being OCH3, 002H5;
R124 is 01_04 -alkyl, such as CH3 or 02H5, or 01-04-alkoxy-01-04-alkyl, such as methoxyme-thyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, with R124 in particular being me-thyl:.
In more preferred embodiment, R12 is in particular a radical of the formula (A"), e.g. (A"-a) or (A11-b) #1.. R123 .0 R123 c.0".1 (A11) 0". (All-a) --R124 (A11-b) wherein # indicates the point of attachment to T and wherein R121, R122, R123and R124 are as de-fined above and wherein R121, R122, R123and R124 independently of each other and especially in combination preferably have the following meanings:
R121 is 01204_ alkoxy, in particular 00H3 or 002H5;
R122 is 01-04-alkoxy, such as 00H3, 002H5, n-propoxyx or isopropoxy, or 03-04-alkenyloxy, such as allyloxy, with R122 in particular being 00H3, 002H5 or n-propoxy;
R123 is OH, 01-04-alkoxy, such as 00H3 or 002H5, or 03-04-alkenyloxy, such as allyloxy, with R123 in particular being 00H3 or 002H5;
R124 is 01_04 -alkyl, such as CH3 or 02H5, or 01-04-alkoxy-01-04-alkyl, such as methoxyme-thyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, with R124 in particular being methyl.
Particular examples of radicals R12 are the following radicals A11-1, A11-la, A"-lb, A"-2, A11-2a, 18,11-2b, A11-3, A11-3a and A11-3b:
H300, OCH3 H3co OCH3 H3co OCH3 #.ØocH3 #1.0-NocH3 #.0-iocH3 o o o c H3 l_ia) 'C H3 (A11_1 b) 'c H3 H300, 002H5 H3C0.. 0C2H5 H300, 002H5 '.
#sAA-0-=mOCH3 # 11.0m1OCH3 # 4 _)¨mOCH3 0 , : 0 C H3 o .' (A11-2) (A11-2a) 0H3 (A11-2b) C H3 H3C0 0¨(n-03H7) H3C0 9¨(n-C3H7) H300, 9¨(n-03H7) #4 _>-=OCH3 #1Ø10CH3 #.-0-.0CH3 (A11-3) CH3 (A11-3a) CH3 (A11-3b) C H3 Particularly preferred compounds of formula I are compounds wherein, A is N or CRA;
G is N or CRB;
Q is NH or NCH3 R is H or 01-06-alkyl, preferably CH3;
RA is H or N(CH3)2;
RB is H or CH3;
Ar is Ar-2;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein X-Y-Z-T
is selected from X-Y-Z-T-1, X-Y-Z-T-2, X-Y-Z-T-3, X-Y-Z-T-4, X-Y-Z-T, X-Y-Z-T-9, X-Y-Z-T-13, X-Y-Z-T-16, X-Y-Z-T-17, X-Y-Z-T-18, and X-Y-Z-T-19;
R11 is R11-1 or R11-10;
R12 is formula A11-1;
Also particularly preferred compounds of formula I are compounds of formula I.a to I.p, wherein D
is R11 or R12, wherein R11 is selected from R11-1 to R11-29, and R12 is selected from (A11-1a), (A11-1b), (A11-2a), (A11-2b), (A11-3a), and (A11-310).
R Rxa RYa D R Rxa RYa D
Al\l'NNII\ N N T
I A N' y 'IR
Ar, G Rxb LWxb Q Nr S---1 Ar, G R S
I.a Q N' I.b Rya R D
R Rxc RYa D
ArNNNN110 Ai N(L /
N
I N 1"__...N0 At-, G Rxa s"--/ Ar-,'G Rxa Rxb I.d S...t Q N' I.d QN
D R RYa D
R Rxc RYa /
ArN NIN1 Ar1)-rNNN\O
I
Ar, G S S-_/ Ar, G S e S
Q N Q N' 'IR
Le I.f R Rxc RYa D R Rxa RYc D
/
/ ANlyr\I-N 0 AN'')(NN-N 1 1 ......t Ar, G Rxb Ar, G 0 S Q N' Q N' I.g I.h R RYa 0 R Rxa RYc Rxa1 S
ANN'. ---1 Ar..Ny0'ID
I
Ar, G Rxb N.....D Ar, G Rxb 0 Q N' Q N' I.i I.j R Rxa RYc ----\ R Rxa RYa D
N-D
I
A)yYLNN-1 AN- y"-RT
Ar, G Rxb 1 0 Ar, G Rxb Q N Q N' I.k 1.1 c R Rxa Rxb Rya R RY D D
I i i N N NN "2 N N
A y ).r -I- \O A
I xa Rxbr\r Ac G Rxa 0 Ar S--/ , G R S
Q N' Q N' I.m I.n Rya D R Rxa RYc /
ARI C)NNL\jt() AND
I
Rxb Rxb Ar, G Rxa S Ar, G
Q N' Q N' 1.0 I.p wherein, Ar is Arl, Ar2, Ar3, Arl, Ar5, Ar6, Ar7, Ar8, Ar9, Arlo, Aril, or Ar12;
Q is NH, NCH3, or 0;
A is N or CH;
G is N, CH, 0-CH3, or 0-01;
R is H, CH3, and 01;
D is R11-1, R11-2, R11-3, R11-4., R11-5, R11-6, R11-7, R11-8, R11-9, R11_10, R11-11, R11-12, R11_13, R11-14, R11-15, R11-16, R11-17, R11-18, R11-19, R11-20, R11-21, R11-22, R11-23, R11-24, R11-25, R11-26, R11-27, R11-28, R11-29, (A11_1a), (A11_1b), (A11_2a), (A11-2b), (A11----obi)-, or (A11-3b);
Rxa iS H or CH3;
Rxb is H or CH3;
Rxb is H or CH3;
RYa is H or CH3;
RYc is H or CH3;
RT is H or CH3, and Re is CH3 or CH2Ph.
Particular compounds of formula I are the compounds of the formulae I.a to I.o that are compiled in the following tables. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Table al. Compounds of formula I.a in which Rxa iS H, Rxb is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.2. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.3. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.4. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, and the .. combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.5. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.6. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.7. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.8. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.9. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.10. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table all. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.12. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.13. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.14. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.15. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.16. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.17. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.18. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.19. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.20. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.21. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.22. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, 5 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.23. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.24. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
10 Table a.25. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.26. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.27. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, and 15 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.28. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.29. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table a.30. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.31. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.32. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and 25 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.33. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.34. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
riy N N N, NN 0 N N N
_t0 N 1._.t0 y - -1- \N yL l S S S
'Re S 0 S
Rxa RYc # Rxa RYao--\s Rxa RYc \.11 N N VYLNI'N vy 0, Rxb 0 s N¨# Rxb 0 0 Rxa RYc xa Yc RYc #
R R 1#
I I i I\L /N¨# 0y N T Ny N N
_NI
VYLNr y o Rxb 0 Rxb 0 Rxa 0 S
RYc T #
\
Rxa RYc INiy RN RYa H
N / .yL 0 # N' y # \o NI 1-1 ' y NI,I.R' T
0 S Rxa Rxb S
Rxb Rxa Rxb Rya #
\XL Nj N' ,RT
,Rxa,\Rxb sy lo XYZT-19 Also particularly preferred X-Y-Z-T are formulas XYZT-1 to XYZT-16;
Also particularly preferred X-Y-Z-T are formulas XYZT-17 to XYZT-19;
In one embodiment, R11 01-06-alkyl, 01-06-haloalkyl, 02-06-alkenyl, 02-06-alkynyl, 01-06-alkoxy-01-04-alkyl, 03-06-cycloalkyl, 03-06-cycloalkyl-C1-04-alkyl, C1-04-alkyl-03-06-cycloalkoxy, which are unsubstituted or substituted with halogen, aryl, arylcarbonyl, aryl-CI-at-alkyl, aryloxy-C1-04-alkyl, hetaryl, carbonylhetaryl, 01-04-alkyl-hetaryl and 01-04-alkyl-hetaryloxy, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl.
In more preferred embodiment, R11 01-06-alkyl, 02-06-alkenyl, 02-06-alkynyl, 03-06-cycloalkyl, which are unsubstituted or substituted with halogen, aryl, arylcarbonyl, aryl-CI-at-alkyl, aryloxy-C1-04-alkyl, hetaryl, carbonylhetaryl, 01-04-alkyl-hetaryl and 01-04-alkyl-hetaryloxy, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl.
In most preferred embodiment, R11 aryl, aryl-CI-at-alkyl, hetaryl, or hetaryl-01-04-alkyl, wherein the rings are unsubstituted or substituted with Rg and where hetaryl in hetaryl or hetaryl-01-04-alkyl, is preferably a 5- or 6-membered monocyclic hetaryl such as pyridyl, pyrimidinyl, pyridazinyl, pyr-rolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl which is unsubstituted or substituted with Rg.
Examples of particularly preferred radicals R11 are the radicals R11-1 to R11-29 summarized in Ta-5 ble B below.
Table B: Examples of radicals R11 R11-1 R11-11 F F ________________________ -CH el R11_20 N
!
H3C'O
C
R11-2 R11_12 I CI R11_21 lel Or ;ICI
F
I
F
F CI
)1,1 a CI CH3 R11-23 el I
ci ocH3 I
H3C. R11-24 a\
F
CI CI
F
R11-6 =A, R11_16 F R11_25 \`1, I I
F
H3CCH3-'CH3 el CI R11-17 H3C 0 Br R11_26 F F
lei Cl R11_27 H3C 0 CH3 !NJ:c H3 R11-28 I I
F
I. F R11_19 !NCH3 jrc.._õ,......H3 .,...."
C.
R11_10 H3 F
e IA
- .3 In one embodiment, R12 is a radical of the formula (A1), (A1) wherein # indicates the point of attachment to T and wherein R121, R122, R123and R124 are as de-fined above and wherein R121, R122, R123and R124 independently of each other and especially in combination preferably have the following meanings:
Ri2i is 01204_ alkoxy, in particular OCH3, 002H5;
R122 is 01-04-alkoxy, such as OCH3, 002H5, n-propoxyx or isopropoxy, or 03-04-alkenyloxy, such as allyloxy, with R122 in particular being OCH3, 002H5, or n-propoxy;
R123 is OH, 01-04-alkoxy, such as OCH3, 002H5õ or 03-04-alkenyloxy, such as allyloxy, with R123 in particular being OCH3, 002H5;
R124 is 01_04 -alkyl, such as CH3 or 02H5, or 01-04-alkoxy-01-04-alkyl, such as methoxyme-thyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, with R124 in particular being me-thyl:.
In more preferred embodiment, R12 is in particular a radical of the formula (A"), e.g. (A"-a) or (A11-b) #1.. R123 .0 R123 c.0".1 (A11) 0". (All-a) --R124 (A11-b) wherein # indicates the point of attachment to T and wherein R121, R122, R123and R124 are as de-fined above and wherein R121, R122, R123and R124 independently of each other and especially in combination preferably have the following meanings:
R121 is 01204_ alkoxy, in particular 00H3 or 002H5;
R122 is 01-04-alkoxy, such as 00H3, 002H5, n-propoxyx or isopropoxy, or 03-04-alkenyloxy, such as allyloxy, with R122 in particular being 00H3, 002H5 or n-propoxy;
R123 is OH, 01-04-alkoxy, such as 00H3 or 002H5, or 03-04-alkenyloxy, such as allyloxy, with R123 in particular being 00H3 or 002H5;
R124 is 01_04 -alkyl, such as CH3 or 02H5, or 01-04-alkoxy-01-04-alkyl, such as methoxyme-thyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, with R124 in particular being methyl.
Particular examples of radicals R12 are the following radicals A11-1, A11-la, A"-lb, A"-2, A11-2a, 18,11-2b, A11-3, A11-3a and A11-3b:
H300, OCH3 H3co OCH3 H3co OCH3 #.ØocH3 #1.0-NocH3 #.0-iocH3 o o o c H3 l_ia) 'C H3 (A11_1 b) 'c H3 H300, 002H5 H3C0.. 0C2H5 H300, 002H5 '.
#sAA-0-=mOCH3 # 11.0m1OCH3 # 4 _)¨mOCH3 0 , : 0 C H3 o .' (A11-2) (A11-2a) 0H3 (A11-2b) C H3 H3C0 0¨(n-03H7) H3C0 9¨(n-C3H7) H300, 9¨(n-03H7) #4 _>-=OCH3 #1Ø10CH3 #.-0-.0CH3 (A11-3) CH3 (A11-3a) CH3 (A11-3b) C H3 Particularly preferred compounds of formula I are compounds wherein, A is N or CRA;
G is N or CRB;
Q is NH or NCH3 R is H or 01-06-alkyl, preferably CH3;
RA is H or N(CH3)2;
RB is H or CH3;
Ar is Ar-2;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein X-Y-Z-T
is selected from X-Y-Z-T-1, X-Y-Z-T-2, X-Y-Z-T-3, X-Y-Z-T-4, X-Y-Z-T, X-Y-Z-T-9, X-Y-Z-T-13, X-Y-Z-T-16, X-Y-Z-T-17, X-Y-Z-T-18, and X-Y-Z-T-19;
R11 is R11-1 or R11-10;
R12 is formula A11-1;
Also particularly preferred compounds of formula I are compounds of formula I.a to I.p, wherein D
is R11 or R12, wherein R11 is selected from R11-1 to R11-29, and R12 is selected from (A11-1a), (A11-1b), (A11-2a), (A11-2b), (A11-3a), and (A11-310).
R Rxa RYa D R Rxa RYa D
Al\l'NNII\ N N T
I A N' y 'IR
Ar, G Rxb LWxb Q Nr S---1 Ar, G R S
I.a Q N' I.b Rya R D
R Rxc RYa D
ArNNNN110 Ai N(L /
N
I N 1"__...N0 At-, G Rxa s"--/ Ar-,'G Rxa Rxb I.d S...t Q N' I.d QN
D R RYa D
R Rxc RYa /
ArN NIN1 Ar1)-rNNN\O
I
Ar, G S S-_/ Ar, G S e S
Q N Q N' 'IR
Le I.f R Rxc RYa D R Rxa RYc D
/
/ ANlyr\I-N 0 AN'')(NN-N 1 1 ......t Ar, G Rxb Ar, G 0 S Q N' Q N' I.g I.h R RYa 0 R Rxa RYc Rxa1 S
ANN'. ---1 Ar..Ny0'ID
I
Ar, G Rxb N.....D Ar, G Rxb 0 Q N' Q N' I.i I.j R Rxa RYc ----\ R Rxa RYa D
N-D
I
A)yYLNN-1 AN- y"-RT
Ar, G Rxb 1 0 Ar, G Rxb Q N Q N' I.k 1.1 c R Rxa Rxb Rya R RY D D
I i i N N NN "2 N N
A y ).r -I- \O A
I xa Rxbr\r Ac G Rxa 0 Ar S--/ , G R S
Q N' Q N' I.m I.n Rya D R Rxa RYc /
ARI C)NNL\jt() AND
I
Rxb Rxb Ar, G Rxa S Ar, G
Q N' Q N' 1.0 I.p wherein, Ar is Arl, Ar2, Ar3, Arl, Ar5, Ar6, Ar7, Ar8, Ar9, Arlo, Aril, or Ar12;
Q is NH, NCH3, or 0;
A is N or CH;
G is N, CH, 0-CH3, or 0-01;
R is H, CH3, and 01;
D is R11-1, R11-2, R11-3, R11-4., R11-5, R11-6, R11-7, R11-8, R11-9, R11_10, R11-11, R11-12, R11_13, R11-14, R11-15, R11-16, R11-17, R11-18, R11-19, R11-20, R11-21, R11-22, R11-23, R11-24, R11-25, R11-26, R11-27, R11-28, R11-29, (A11_1a), (A11_1b), (A11_2a), (A11-2b), (A11----obi)-, or (A11-3b);
Rxa iS H or CH3;
Rxb is H or CH3;
Rxb is H or CH3;
RYa is H or CH3;
RYc is H or CH3;
RT is H or CH3, and Re is CH3 or CH2Ph.
Particular compounds of formula I are the compounds of the formulae I.a to I.o that are compiled in the following tables. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Table al. Compounds of formula I.a in which Rxa iS H, Rxb is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.2. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.3. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.4. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, and the .. combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.5. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.6. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.7. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.8. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.9. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.10. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table all. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.12. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.13. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.14. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.15. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.16. Compounds of formula I.a in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.17. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.18. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.19. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.20. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.21. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.22. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, 5 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.23. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.24. Compounds of formula I.a in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
10 Table a.25. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.26. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.27. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, and 15 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.28. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.29. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table a.30. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.31. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.32. Compounds of formula I.a in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and 25 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.33. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.34. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table a.35. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.36. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.37. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-35 CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.38. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.39. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.40. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.41. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.42. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.43. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.44. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.45. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.46. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.47. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.48. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.1. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.2. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, RT is H, .. and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.3. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.4. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.5. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.6. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.7. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.8. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.9. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A
is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.10. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.11. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.12. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, RT is H, .. and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.13. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.14. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.15. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.16. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.17. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.18. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.19. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.20. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.21. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.22. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.23. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.24. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.25. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.26. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.27. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.28. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.29. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.30. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.31. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.32. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.33. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.34. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.35. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.36. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.37. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.38. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.39. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.40. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.41. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.42. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.43. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.44. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.45. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.46. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.47. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-Cl, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.48. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.49. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.50. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.51. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.52. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.53. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.54. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.55. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.56. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.57. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.58. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.59. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.60. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.61. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.62. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.63. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.64. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.65. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.66. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.67. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.68. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.69. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.70. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.71. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.72. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.73. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT
5 .. is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.74. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.75. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is 10 CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.76. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.77. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-15 ble A.
Table b.78. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.79. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table b.80. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.81. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
25 Table b.82. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.83. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.84. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, RT is 30 CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.85. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.86. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, 35 RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.87. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
40 Table b.88. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.89. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.90. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.91. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.92. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.93. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.94. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.95. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-C!, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.96. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table c.1. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.2. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is CH, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.3. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.4. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.5. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is C-CH3, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.6. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is C-CH3, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.7. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.8. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.9. Compounds of formula I.c in which Rxa iS CH3, RYa is H, A is CH, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.10. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.11. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.12. Compounds of formula I.c in which Rxa iS CH3, RYa is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.13. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.14. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.15. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.16. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.17. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.18. Compounds of formula I.c in which Rxa is H, RYa iS CH3, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.19. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.20. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.21. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.22. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.23. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.24. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.1. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.2. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.3. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.4. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.5. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.6. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, RYa is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.7. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is H, A is CH, G is C-Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.8. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.9. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.10. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.11. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.12. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.13. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.14. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.15. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.16. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.17. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.18. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.19. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.20. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.21. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.22. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.23. Compounds of formula I.d in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.24. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.25. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.26. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.27. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.28. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.29. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.30. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.31. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.32. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is .. C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.33. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.34. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.35. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.36. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.37. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.38. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.39. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.40. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.41. pounds of the formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table d.42. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.43. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.44. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is 10 N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.45. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.46. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is 15 C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.47. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.48. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is 20 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.49. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.50. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
25 Table d.51. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, RYa is H, A is CH, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.52. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.53. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is CH, G
30 is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.54. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
35 Table d.55. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.56. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table d.57. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.58. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.59. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.60. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.61. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.62. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.63. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.64. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is .. C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.65. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.66. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.67. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.68. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.69. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.70. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.71. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.72. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.73. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.74. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.75. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-.. ble A.
Table d.76. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.77. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is .. CH, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.78. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.79. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is CH, G is 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.80. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table el. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.2. Compounds of formula I.e in which Rxc is H, Rya is H, A is N, G is CH, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table e.3. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G
is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.4. Compounds of formula I.e in which Rxc is H, Rya is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.5. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G is 0-CH3, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.6. Compounds of formula I.e in which Rxc is H, RYa is H, A is N, G is 0-CH3, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.7. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G is 0-01, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.8. Compounds of formula I.e in which Rxc is H, RYa is H, A is N, G is 0-01, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.9. Compounds of formula I.e in which Rxc is CH3, Rya is H, A is CH, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.10. Compounds of formula I.e in which Rxc is CH3, Rya is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.11. Compounds of formula I.e in which Rxc is CH3, RYa iS H, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.12. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.13. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.14. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.15. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.16. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.17. Compounds of formula I.e in which Rxc is H, RYa iS CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.18. Compounds of formula I.e in which Rxc is H, RYa iS CH3, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.19. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.20. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.21. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.22. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.23. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.24. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.1. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.2. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.3. Compounds of formula I.f in which Re Re is CH2Ph, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.4. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.5. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.6. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.7. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.8. Compounds of formula I.f in which Re Re is CH2Ph, RYa is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.9. Compounds of formula I.f in which Reis CH3, Rya is H, A iS CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.10. Compounds of formula I.f in which Reis CH3, Rya is H, A iS N, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.11. Compounds of formula I.f in which Re is CH3, Rya is H, A is CH, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.12. Compounds of formula I.f in which Reis CH3, Rya is H, A iS N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.13. Compounds of formula I.f in which Reis CH3, Rya is H, A iS CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.14. Compounds of formula I.f in which Reis CH3, Rya is H, A iS N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.15. Compounds of formula I.f in which Reis CH3, Rya is H, A iS CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.16. Compounds of formula I.f in which Reis CH3, RYa iS H, A is N, G is C-CI, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.17. Compounds of formula I.f in which Re iS CH2Ph, RYa iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.18. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.19. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.20. Compounds of formula I.f in which Re is CH2Ph, RYa is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.21. Compounds of formula I.f in which Re is CH2Ph, RYa is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.22. Compounds of formula I.f in which Re is CH2Ph, RYa is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.23. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.24. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.1. Compounds of formula I.g in which Rxc is H, Rya is H, A is CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.2. Compounds of formula I.g in which Rxc is H, Rya is H, A is N, G is CH, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.3. Compounds of formula I.g in which Rxc is H, Rya is H, A is CH, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.4. Compounds of formula I.g in which Rxc is H, RYa is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.5. Compounds of formula I.g in which Rxc is H, RYa is H, A is CH, G is C-CH3, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table g.6. Compounds of formula I.g in which Rxc is H, RYa is H, A is N, G is C-CH3, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.7. Compounds of formula I.g in which Rxc is H, RYa is H, A is CH, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.8. Compounds of formula I.g in which Rxc is H, RYa is H, A is N, G is C-CI, and the combi-10 nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.9. Compounds of formula I.g in which Rxc is CH3, RYa is H, A is CH, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.10. Compounds of formula I.g in which Rxc is CH3, RYa is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
15 Table g.11. Compounds of formula I.g in which Rxc is CH3, RYa is H, A is CH, G is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.12. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.13. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is CH, G
is C-CH3, and the 20 combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.14. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.15. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
25 Table g.16. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.17. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.18. Compounds of formula I.g in which Rxc is H, RYa iS CH3, A is N, G
is CH, and the com-30 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.19. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.20. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
35 Table g.21. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.22. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.23. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G
is C-CI, and the 40 combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.24. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.1. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.2. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.3. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.4. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.5. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.6. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.7. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.8. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.9. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.10. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.11. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.12. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.13. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.14. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.15. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.16. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.17. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.18. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.19. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.20. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.21. Compounds of formula I.h in which Rxa iS H, Rxb is CH3, RYc iS H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.22. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.23. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.24. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.25. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.26. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.27. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.28. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.29. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.30. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.31. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.32. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.33. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.34. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.35. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.36. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.37. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.38. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.39. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.40. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.41. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.42. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.43. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.44. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.45. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.46. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.47. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.48. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.1. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.2. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.3. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.4. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.5. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.6. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.7. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.8. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.9. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.10. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.11. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.12. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.13. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.14. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.15. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.16. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.17. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.18. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.19. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.20. Compounds of formula I.i in which Rxa is H, Rxb is CH3, RYa is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.21. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.22. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.23. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.24. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.25. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.26. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.27. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.28. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.29. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.30. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.31. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.32. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.33. Compounds of formula I.i in which Rxa is CH3, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.34. Compounds of formula I.i in which Rxa is CH3, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.35. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.36. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, and 5 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.37. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.38. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
10 Table i.39. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.40. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.41. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, 15 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.42. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.43. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table i.44. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.45. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.46. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, 25 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.47. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.48. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table j.1. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.2. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.3. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the 35 combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.4. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.5. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table j.6. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.7. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.8. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.9. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.10. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.11. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.12. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.13. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.14. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.15. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.16. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.17. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.18. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.19. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.20. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.21. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.22. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.23. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.24. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.25. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.26. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.27. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.28. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.29. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.30. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.31. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is 0-Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.32. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.33. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.34. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.35. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.36. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.37. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.38. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.39. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.40. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.41. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.42. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.43. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.44. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.45. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.46. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.47. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.48. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.1. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.2. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.3. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.4. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the .. combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.5. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.6. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.7. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.8. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.9. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A
is CH, G is CH, and .. the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.10. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.11. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.12. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.13. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.14. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, .. and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.15. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.16. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table k.17. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.18. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.19. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and .. the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.20. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.21. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is CH, G is C-CH3CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table k.22. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.23. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.24. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.25. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.26. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.27. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.28. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.29. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.30. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.31. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.32. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.33. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.34. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.35. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.36. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.37. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.38. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.39. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.40. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.41. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.42. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is CH, 5 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.43. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.44. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
10 Table k.45. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.46. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.47. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-15 Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.48. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.1. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table 1.2. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.3. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.4. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is N, G is N, RT is H, and 25 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.5. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.6. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table 1.7. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A is CH, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.8. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.9. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A
is CH, G is CH, RT is 35 H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.10. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.11. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table 1.12. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.13. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.14. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.15. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.16. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.17. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.18. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.19. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.20. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.21. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.22. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.23. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.24. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.25. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.26. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.27. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.28. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.29. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.30. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.31. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.32. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.33. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.34. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.35. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.36. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.37. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.38. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.39. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.40. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-C1, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.41. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.42. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.43. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.44. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.45. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.46. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.47. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.48. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.49. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.50. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.51. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.52. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.53. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.54. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.55. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.56. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.57. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.58. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.59. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.60. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, RT is .. CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.61. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.62. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.63. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.64. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.65. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.66. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.67. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.68. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.69. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.70. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.71. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.72. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.73. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.74. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.75. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.76. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.77. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.78. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.79. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.80. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.81. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.82. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.83. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.84. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.85. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.86. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.87. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.88. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is C-C1, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.89. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.90. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is N, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.91. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is CH, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.92. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is N, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.93. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table 1.94. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is 0-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.95. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-10 ble A.
Table 1.96. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table m.1. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is CH, and the com-15 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.2. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.3. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table m.4. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.5. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.6. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is C-CH3, and the com-25 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.7. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is C-CI, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.8. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table m.9. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.10. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.11. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is CH, G
is N, and the com-35 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.12. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.13. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table m.14. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.15. Compounds of formula I.m in which Rxa iS CH3, RYc iS H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.16. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.17. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.18. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.19. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.20. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.21. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.22. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.23. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.24. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.1. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.2. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.3. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.4. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa iS
H, A iS N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.5. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.6. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.7. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.8. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.9. Compounds of formula I.n in which "1-Rxa is CH3, "1-Rxb is H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.10. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.11. Compounds of formula I.n in which "1-RxaiS CH3, "1-Rxb iS H, "2-RxaiS H, "2-RxbiS H, Rya is H, Rya is H, A iS CH, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.12. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.13. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, Rya is H, A iS CH, G is C-CH3, and the combination of R, Q, Ar and D
for a compound cor-responds to each line of Table A.
Table n.14. Compounds of formula I.n in which "1-RxaiS CH3, "1-Rxb iS H, "2-RxaiS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is C-CH3, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.15. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, RYaiS H, A iS CH, G is C-CI, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.16. Compounds of formula I.n in which "1-RxaiS CH3, "1-Rxb iS H, "2-RxaiS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is C-CI, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.17. Compounds of formula I.n in which "1-Rxa iS H, "1-RxbiS H, "2-Rxa iS CH3, "2-Rxb iS H, Rya is H, RYaiS H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.18. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.19. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A iS CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.20. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.21. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A iS CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.22. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb iS H, RY is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.23. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb iS H, Rya is H, A iS CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.24. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb iS H, RY is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.25. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.26. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.27. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.28. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.29. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.30. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.31. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A iS CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.32. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.33. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.34. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.35. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.36. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2_Rxb is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.37. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is CH, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.38. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is N, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.39. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is CH, G is 0-01, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.40. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, RYa is H, A is N, G is 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.41. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.42. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, RYa is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.43. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.44. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, RYa is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.45. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is CH, G is CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.46. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is N, G is CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.47. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is CH, G is 0-01, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.48. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is 0-01, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.49. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.50. Compounds of formula I.n in which "1-Rxa is CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is 5 H, Rya is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.51. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
10 Table n.52. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.53. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, RYa is H, RYa is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound 15 corresponds to each line of Table A.
Table n.54. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound cor-responds to each line of Table A.
Table n.55. Compounds of formula I.n in which "1-Rxa is CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is 20 H, Rya is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound cor-responds to each line of Table A.
Table n.56. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
25 Table n.57. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.58. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds 30 to each line of Table A.
Table n.59. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa is CH3, "2-Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.60. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is 35 CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.61. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
40 Table n.62. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, RYa is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.63. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.64. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, RYa is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.65. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.66. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.67. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, RYa is CH3, RYa is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.68. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.69. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, RYa is CH3, RYa is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.70. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is .. H, Rya is CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.71. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.72. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.73. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.74. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.75. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.76. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.77. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D
for a compound cor-responds to each line of Table A.
Table n.78. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.79. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.80. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, RYa is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table o.1. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.2. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table 0.3. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.4. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.5. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.6. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.7. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.8. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.9. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.10. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is N, G is CH, and .. the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.11. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.12. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.13. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.14. Compounds of formula I.o in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.15. Compounds of formula I.o in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.16. Compounds of formula I.o in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.17. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.18. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.19. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.20. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.21. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.22. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.23. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.24. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.25. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.26. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.27. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.28. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.29. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.30. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.31. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.32. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.33. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.34. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.35. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.36. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.37. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.38. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.39. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.40. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.41. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.42. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.43. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.44. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.45. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.46. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.47. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.48. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.1. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.2. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.3. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.4. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.5. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.6. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.7. Compounds of formula I.p in which Rxa iS H, Rxb is H, RYc iS H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.8. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table p.9. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.10. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.11. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and 10 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.12. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.13. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
15 Table p.14. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.15. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.16. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and 20 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.17. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.18. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
25 Table p.19. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.20. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.21. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-30 CH3CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table p.22. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.23. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-CI, 35 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.24. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.25. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table p.26. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.27. Compounds of formula I.p in which Rxa iS H, Rxb is H, RY iS CH3, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.28. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.29. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.30. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.31. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.32. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.33. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.34. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.35. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.36. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.37. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.38. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.39. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.40. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.41. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.42. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.43. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.44. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.45. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.46. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.47. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is C-Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.48. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table A:
Line R Q Ar D Line R Q Ar D
1 H NH Arl R11-1 36 H NH Ar2 R11-1 2 H NH Arl R11-2 37 H NH Ar2 R11-2 3 H NH Arl R11-3 38 H NH Ar2 R11-3 4 H NH Arl R11-4 39 H NH Ar2 R11-4 H NH Arl R11-5 40 H NH Ar2 R11-5 6 H NH Arl R11-6 41 H NH Ar2 R11-6 7 H NH Arl R11-7 42 H NH Ar2 R11-7 8 H NH Arl R11-8 43 H NH Ar2 R11-8 9 H NH Arl R11-9 44 H NH Ar2 R11-9 H NH Arl R11-10 45 H NH Ar2 R11-10 11 H NH Arl R11-11 46 H NH Ar2 R11-11 12 H NH Arl R11-12 47 H NH Ar2 R11-12 13 H NH Arl R11-13 48 H NH Ar2 R11-13 14 H NH Arl R11-14 49 H NH Ar2 R11-14 H NH Arl R11-15 50 H NH Ar2 R11-15 16 H NH Arl R11-16 51 H NH Ar2 R11-16 17 H NH Arl R11-17 52 H NH Ar2 R11-17 18 H NH Arl R11-18 53 H NH Ar2 R11-18 19 H NH Arl R11-19 54 H NH Ar2 R11-19 H NH Arl R11-20 55 H NH Ar2 R11-20 21 H NH Arl R11-21 56 H NH Ar2 R11-21 22 H NH Arl R11-22 57 H NH Ar2 R11-22 23 H NH Arl R11-23 58 H NH Ar2 R11-23 24 H NH Arl R11-24 59 H NH Ar2 R11-24 H NH Arl R11-25 60 H NH Ar2 R11-25 26 H NH Arl R11-26 61 H NH Ar2 R11-26 27 H NH Arl R11-27 62 H NH Ar2 R11-27 28 H NH Arl R11-28 63 H NH Ar2 R11-28 29 H NH Arl R11-29 64 H NH Ar2 R11-29 H NH Arl A11-la 65 H NH Ar2 A11-la
Table a.36. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.37. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-35 CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.38. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.39. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.40. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.41. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.42. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.43. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.44. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.45. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.46. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.47. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table a.48. Compounds of formula I.a in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.1. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.2. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, RT is H, .. and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.3. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.4. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.5. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.6. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.7. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.8. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.9. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A
is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.10. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.11. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.12. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, RT is H, .. and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.13. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.14. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.15. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.16. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.17. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.18. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.19. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.20. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.21. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.22. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.23. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.24. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.25. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.26. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.27. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.28. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.29. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.30. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.31. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.32. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.33. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.34. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.35. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.36. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.37. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.38. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.39. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.40. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.41. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.42. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table b.43. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.44. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.45. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.46. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.47. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-Cl, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.48. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.49. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.50. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.51. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.52. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.53. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.54. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.55. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.56. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.57. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.58. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.59. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.60. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.61. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.62. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.63. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.64. Compounds of formula I.b in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.65. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.66. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.67. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.68. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.69. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.70. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.71. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.72. Compounds of formula I.b in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.73. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT
5 .. is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.74. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.75. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is 10 CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.76. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.77. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-15 ble A.
Table b.78. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.79. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table b.80. Compounds of formula I.b in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.81. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
25 Table b.82. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.83. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.84. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, RT is 30 CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.85. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.86. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, 35 RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.87. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
40 Table b.88. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.89. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.90. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.91. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table b.92. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.93. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.94. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.95. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-C!, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table b.96. Compounds of formula I.b in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table c.1. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.2. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is CH, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.3. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.4. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.5. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is C-CH3, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.6. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is C-CH3, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.7. Compounds of formula I.c in which Rxa is H, Rya is H, A is CH, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.8. Compounds of formula I.c in which Rxa is H, Rya is H, A is N, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.9. Compounds of formula I.c in which Rxa iS CH3, RYa is H, A is CH, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.10. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.11. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.12. Compounds of formula I.c in which Rxa iS CH3, RYa is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.13. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.14. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.15. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.16. Compounds of formula I.c in which Rxa iS CH3, Rya is H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.17. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.18. Compounds of formula I.c in which Rxa is H, RYa iS CH3, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.19. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.20. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.21. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.22. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.23. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table c.24. Compounds of formula I.c in which Rxa is H, Rya is CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.1. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.2. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.3. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.4. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.5. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.6. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, RYa is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.7. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is H, A is CH, G is C-Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.8. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.9. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.10. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.11. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.12. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.13. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.14. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.15. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.16. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.17. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.18. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.19. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.20. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.21. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.22. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.23. Compounds of formula I.d in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.24. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.25. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.26. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.27. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.28. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.29. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.30. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.31. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.32. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is H, A is N, G is .. C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.33. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.34. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.35. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.36. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.37. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.38. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.39. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.40. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.41. pounds of the formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table d.42. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.43. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.44. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is 10 N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.45. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.46. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is 15 C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.47. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.48. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is H, A is N, G is 20 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.49. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.50. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
25 Table d.51. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, RYa is H, A is CH, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.52. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.53. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is CH, G
30 is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.54. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
35 Table d.55. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.56. Compounds of formula I.d in which Rxa iS CH3, Rxb is H, Rxc is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table d.57. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.58. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.59. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.60. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.61. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.62. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.63. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.64. Compounds of formula I.d in which Rxa is H, Rxb is H, Rxc is CH3, Rya is CH3, A is N, G is .. C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.65. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.66. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.67. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.68. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.69. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.70. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.71. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.72. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.73. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.74. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.75. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-.. ble A.
Table d.76. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table d.77. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is .. CH, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.78. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.79. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is CH, G is 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table d.80. Compounds of formula I.d in which Rxa iS CH3, Rxb iS CH3, Rxc iS
CH3, Rya is CH3, A is N, G is 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table el. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.2. Compounds of formula I.e in which Rxc is H, Rya is H, A is N, G is CH, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table e.3. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G
is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.4. Compounds of formula I.e in which Rxc is H, Rya is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.5. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G is 0-CH3, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.6. Compounds of formula I.e in which Rxc is H, RYa is H, A is N, G is 0-CH3, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.7. Compounds of formula I.e in which Rxc is H, Rya is H, A is CH, G is 0-01, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.8. Compounds of formula I.e in which Rxc is H, RYa is H, A is N, G is 0-01, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.9. Compounds of formula I.e in which Rxc is CH3, Rya is H, A is CH, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.10. Compounds of formula I.e in which Rxc is CH3, Rya is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.11. Compounds of formula I.e in which Rxc is CH3, RYa iS H, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.12. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.13. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.14. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.15. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.16. Compounds of formula I.e in which Rxc is CH3, RYa is H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.17. Compounds of formula I.e in which Rxc is H, RYa iS CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.18. Compounds of formula I.e in which Rxc is H, RYa iS CH3, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.19. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.20. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.21. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.22. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.23. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table e.24. Compounds of formula I.e in which Rxc is H, Rya is CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.1. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.2. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.3. Compounds of formula I.f in which Re Re is CH2Ph, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.4. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.5. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.6. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.7. Compounds of formula I.f in which Re is CH2Ph, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.8. Compounds of formula I.f in which Re Re is CH2Ph, RYa is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.9. Compounds of formula I.f in which Reis CH3, Rya is H, A iS CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.10. Compounds of formula I.f in which Reis CH3, Rya is H, A iS N, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.11. Compounds of formula I.f in which Re is CH3, Rya is H, A is CH, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.12. Compounds of formula I.f in which Reis CH3, Rya is H, A iS N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.13. Compounds of formula I.f in which Reis CH3, Rya is H, A iS CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.14. Compounds of formula I.f in which Reis CH3, Rya is H, A iS N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.15. Compounds of formula I.f in which Reis CH3, Rya is H, A iS CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.16. Compounds of formula I.f in which Reis CH3, RYa iS H, A is N, G is C-CI, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.17. Compounds of formula I.f in which Re iS CH2Ph, RYa iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.18. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.19. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.20. Compounds of formula I.f in which Re is CH2Ph, RYa is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.21. Compounds of formula I.f in which Re is CH2Ph, RYa is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.22. Compounds of formula I.f in which Re is CH2Ph, RYa is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.23. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table f.24. Compounds of formula I.f in which Re is CH2Ph, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.1. Compounds of formula I.g in which Rxc is H, Rya is H, A is CH, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.2. Compounds of formula I.g in which Rxc is H, Rya is H, A is N, G is CH, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.3. Compounds of formula I.g in which Rxc is H, Rya is H, A is CH, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.4. Compounds of formula I.g in which Rxc is H, RYa is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.5. Compounds of formula I.g in which Rxc is H, RYa is H, A is CH, G is C-CH3, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table g.6. Compounds of formula I.g in which Rxc is H, RYa is H, A is N, G is C-CH3, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.7. Compounds of formula I.g in which Rxc is H, RYa is H, A is CH, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.8. Compounds of formula I.g in which Rxc is H, RYa is H, A is N, G is C-CI, and the combi-10 nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.9. Compounds of formula I.g in which Rxc is CH3, RYa is H, A is CH, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.10. Compounds of formula I.g in which Rxc is CH3, RYa is H, A is N, G
is CH, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
15 Table g.11. Compounds of formula I.g in which Rxc is CH3, RYa is H, A is CH, G is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.12. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.13. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is CH, G
is C-CH3, and the 20 combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.14. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.15. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
25 Table g.16. Compounds of formula I.g in which Rxc is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.17. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.18. Compounds of formula I.g in which Rxc is H, RYa iS CH3, A is N, G
is CH, and the com-30 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.19. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.20. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
35 Table g.21. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.22. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.23. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is CH, G
is C-CI, and the 40 combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table g.24. Compounds of formula I.g in which Rxc is H, Rya is CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.1. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.2. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.3. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.4. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.5. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.6. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.7. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.8. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.9. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.10. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.11. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.12. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.13. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.14. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.15. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.16. Compounds of formula I.h in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.17. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.18. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.19. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.20. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.21. Compounds of formula I.h in which Rxa iS H, Rxb is CH3, RYc iS H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.22. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.23. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.24. Compounds of formula I.h in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.25. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.26. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.27. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.28. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.29. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.30. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.31. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.32. Compounds of formula I.h in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.33. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.34. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.35. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.36. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.37. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.38. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.39. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.40. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.41. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.42. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.43. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.44. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.45. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.46. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.47. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table h.48. Compounds of formula I.h in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.1. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.2. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.3. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.4. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.5. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.6. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.7. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.8. Compounds of formula I.i in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.9. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.10. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.11. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.12. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.13. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, RYa is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.14. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.15. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.16. Compounds of formula I.i in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.17. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.18. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.19. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.20. Compounds of formula I.i in which Rxa is H, Rxb is CH3, RYa is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.21. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.22. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.23. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.24. Compounds of formula I.i in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.25. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.26. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.27. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.28. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.29. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.30. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.31. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.32. Compounds of formula I.i in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.33. Compounds of formula I.i in which Rxa is CH3, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.34. Compounds of formula I.i in which Rxa is CH3, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.35. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.36. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, and 5 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.37. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.38. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
10 Table i.39. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.40. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.41. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, 15 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.42. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.43. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table i.44. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.45. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.46. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, 25 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.47. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table i.48. Compounds of formula I.i in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table j.1. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.2. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.3. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the 35 combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.4. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.5. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table j.6. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.7. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.8. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.9. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.10. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.11. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.12. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.13. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.14. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.15. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.16. Compounds of formula I.j in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.17. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.18. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.19. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.20. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.21. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.22. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.23. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.24. Compounds of formula I.j in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.25. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.26. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.27. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.28. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.29. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.30. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.31. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is 0-Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.32. Compounds of formula I.j in which Rxa is H, Rxb is H, RYc iS CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.33. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.34. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.35. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.36. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.37. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.38. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.39. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.40. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.41. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.42. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.43. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.44. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.45. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.46. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.47. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table j.48. Compounds of formula I.j in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.1. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.2. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.3. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.4. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the .. combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.5. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.6. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.7. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.8. Compounds of formula I.k in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.9. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A
is CH, G is CH, and .. the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.10. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.11. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.12. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.13. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.14. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, .. and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.15. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.16. Compounds of formula I.k in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table k.17. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.18. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.19. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and .. the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.20. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.21. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is CH, G is C-CH3CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table k.22. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.23. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.24. Compounds of formula I.k in which Rxa is H, Rxb is CH3, RY is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.25. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.26. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.27. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.28. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.29. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.30. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.31. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.32. Compounds of formula I.k in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.33. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.34. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.35. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.36. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.37. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.38. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.39. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.40. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.41. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.42. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is CH, 5 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.43. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.44. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
10 Table k.45. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.46. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.47. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is CH, G is C-15 Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table k.48. Compounds of formula I.k in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.1. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table 1.2. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.3. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.4. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is N, G is N, RT is H, and 25 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.5. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.6. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table 1.7. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A is CH, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.8. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RYa is H, A
is N, G is C-CI, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.9. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A
is CH, G is CH, RT is 35 H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.10. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.11. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table 1.12. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, RYa is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.13. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.14. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.15. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.16. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.17. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.18. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.19. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.20. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.21. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.22. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.23. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.24. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.25. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.26. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.27. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.28. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.29. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.30. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.31. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.32. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.33. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.34. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.35. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.36. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.37. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.38. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.39. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.40. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-C1, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.41. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.42. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.43. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.44. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, RT
is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.45. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.46. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH3, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.47. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.48. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-C1, RT is H, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.49. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.50. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.51. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.52. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.53. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.54. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.55. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.56. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is H, A
is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.57. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.58. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.59. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.60. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is N, RT is .. CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.61. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.62. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.63. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.64. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.65. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.66. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.67. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.68. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, RYa is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.69. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.70. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.71. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.72. Compounds of formula 1.1 in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.73. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.74. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.75. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.76. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.77. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.78. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is C-CH3, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.79. Compounds of formula 1.1 in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.80. Compounds of formula 1.1 in which Rxa is H, Rxb is H, RY is CH3, A
is N, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.81. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.82. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.83. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.84. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is N, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.85. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.86. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.87. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is CH, G is C-C1, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.88. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is H, A is N, G is C-C1, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.89. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is CH, G is CH, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.90. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is N, G is CH, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.91. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is CH, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.92. Compounds of formula 1.1 in which Rxa iS CH3, Rxb is CH3, Rya is CH3, A is N, G is N, RT
is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 1.93. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table 1.94. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is 0-CH3, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table 1.95. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-10 ble A.
Table 1.96. Compounds of formula 1.1 in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, RT is CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table m.1. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is CH, and the com-15 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.2. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is CH, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.3. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
20 Table m.4. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is N, and the combina-tion of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.5. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.6. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is C-CH3, and the com-25 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.7. Compounds of formula I.m in which Rxa is H, RYc is H, A is CH, G is C-CI, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.8. Compounds of formula I.m in which Rxa is H, RYc is H, A is N, G is C-CI, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
30 Table m.9. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.10. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.11. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is CH, G
is N, and the com-35 bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.12. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.13. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table m.14. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.15. Compounds of formula I.m in which Rxa iS CH3, RYc iS H, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.16. Compounds of formula I.m in which Rxa iS CH3, RYc is H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.17. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.18. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.19. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is N, and the com-bination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.20. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is N, and the combi-nation of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.21. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.22. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.23. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is CH, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table m.24. Compounds of formula I.m in which Rxa is H, RYc iS CH3, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.1. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.2. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.3. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.4. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa iS
H, A iS N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.5. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.6. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.7. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.8. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.9. Compounds of formula I.n in which "1-Rxa is CH3, "1-Rxb is H, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.10. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.11. Compounds of formula I.n in which "1-RxaiS CH3, "1-Rxb iS H, "2-RxaiS H, "2-RxbiS H, Rya is H, Rya is H, A iS CH, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.12. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.13. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, Rya is H, A iS CH, G is C-CH3, and the combination of R, Q, Ar and D
for a compound cor-responds to each line of Table A.
Table n.14. Compounds of formula I.n in which "1-RxaiS CH3, "1-Rxb iS H, "2-RxaiS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is C-CH3, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.15. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS H, "2-Rxa iS H, "2-RxbiS H, Rya is H, RYaiS H, A iS CH, G is C-CI, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.16. Compounds of formula I.n in which "1-RxaiS CH3, "1-Rxb iS H, "2-RxaiS H, "2-RxbiS H, Rya is H, Rya is H, A iS N, G is C-CI, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.17. Compounds of formula I.n in which "1-Rxa iS H, "1-RxbiS H, "2-Rxa iS CH3, "2-Rxb iS H, Rya is H, RYaiS H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.18. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.19. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A iS CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.20. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.21. Compounds of formula I.n in which "1-RxaiS H, "1-RxbiS H, "2-RxaiS
CH3, "2-Rxb iS H, Rya is H, A iS CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.22. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb iS H, RY is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.23. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb iS H, Rya is H, A iS CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.24. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb iS H, RY is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.25. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.26. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.27. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.28. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.29. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.30. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, RYa is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.31. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A iS CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.32. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS H, "2-Rxb iS H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.33. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A iS CH, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.34. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A iS N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.35. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.36. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2_Rxb is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.37. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is CH, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.38. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is N, G is 0-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.39. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is H, A is CH, G is 0-01, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.40. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, RYa is H, A is N, G is 0-01, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.41. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.42. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, RYa is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.43. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.44. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, RYa is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.45. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is CH, G is CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.46. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is N, G is CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.47. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb iS
CH3, Rya is CH3, A is CH, G is 0-01, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.48. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is 0-01, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.49. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa iS H, "2-Rxb iS H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.50. Compounds of formula I.n in which "1-Rxa is CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is 5 H, Rya is H, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.51. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
10 Table n.52. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D
for a compound corre-sponds to each line of Table A.
Table n.53. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, RYa is H, RYa is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound 15 corresponds to each line of Table A.
Table n.54. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound cor-responds to each line of Table A.
Table n.55. Compounds of formula I.n in which "1-Rxa is CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is 20 H, Rya is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound cor-responds to each line of Table A.
Table n.56. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
25 Table n.57. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.58. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds 30 to each line of Table A.
Table n.59. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa is CH3, "2-Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.60. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is 35 CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.61. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
40 Table n.62. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, RYa is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.63. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.64. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, RYa is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.65. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb iS CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.66. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.67. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, RYa is CH3, RYa is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.68. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.69. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, RYa is CH3, RYa is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.70. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is .. H, Rya is CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.71. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.72. Compounds of formula I.n in which "1-Rxa iS CH3, "1-Rxb is CH3, "2-Rxa is H, "2-Rxb is H, Rya is CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table n.73. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a com-pound corresponds to each line of Table A.
Table n.74. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.75. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.76. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.77. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D
for a compound cor-responds to each line of Table A.
Table n.78. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.79. Compounds of formula I.n in which "1-Rxa iS H, "1-Rxb iS H, "2-Rxa iS CH3, "2-Rxb is CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table n.80. Compounds of formula I.n in which "1-Rxa is H, "1-Rxb is H, "2-Rxa iS CH3, "2-Rxb is CH3, RYa is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corre-sponds to each line of Table A.
Table o.1. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.2. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
.. Table 0.3. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.4. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.5. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.6. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.7. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.8. Compounds of formula I.o in which Ris H, Rxb is H, Rya H, A is N, G
is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.9. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.10. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is N, G is CH, and .. the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.11. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.12. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.13. Compounds of formula I.o in which Rxa iS CH3, Rxbis H, Rya H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.14. Compounds of formula I.o in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.15. Compounds of formula I.o in which Rxa iS CH3, Rxb is H, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.16. Compounds of formula I.o in which Rxa iS CH3, Rxb is H, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.17. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.18. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.19. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.20. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.21. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-C2H5, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.22. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.23. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.24. Compounds of formula I.o in which Rxa is H, Rxb is CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.25. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.26. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.27. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.28. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.29. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.30. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.31. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.32. Compounds of formula I.o in which Rxa is H, Rxb is H, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.33. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.34. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.35. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.36. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.37. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.38. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table 0.39. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.40. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.41. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.42. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.43. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.44. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.45. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.46. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.47. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table o.48. Compounds of formula I.o in which Rxa iS CH3, Rxb iS CH3, Rya is CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.1. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.2. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.3. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.4. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.5. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.6. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.7. Compounds of formula I.p in which Rxa iS H, Rxb is H, RYc iS H, A
is CH, G is CCI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.8. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc is H, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
5 Table p.9. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.10. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.11. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is N, and 10 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.12. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.13. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
15 Table p.14. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.15. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.16. Compounds of formula I.p in which Rxa iS CH3, Rxb is H, RYc is H, A is N, G is C-CI, and 20 the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.17. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.18. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
25 Table p.19. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.20. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.21. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-30 CH3CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Ta-ble A.
Table p.22. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.23. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is CH, G is C-CI, 35 and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.24. Compounds of formula I.p in which Rxa is H, Rxb is CH3, RYc is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.25. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc iS CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
40 Table p.26. Compounds of formula I.p in which Rxa is H, Rxb is H, RYc iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.27. Compounds of formula I.p in which Rxa iS H, Rxb is H, RY iS CH3, A
is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.28. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.29. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.30. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.31. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.32. Compounds of formula I.p in which Rxa is H, Rxb is H, RY iS CH3, A
is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.33. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.34. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.35. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.36. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.37. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.38. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.39. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is CH, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.40. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY is H, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.41. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.42. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is N, G is CH, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.43. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.44. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is N, G is N, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.45. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.46. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is N, G is C-CH3, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.47. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RY iS
CH3, A is CH, G is C-Cl, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table p.48. Compounds of formula I.p in which Rxa iS CH3, Rxb iS CH3, RYc iS
CH3, A is N, G is C-CI, and the combination of R, Q, Ar and D for a compound corresponds to each line of Table A.
Table A:
Line R Q Ar D Line R Q Ar D
1 H NH Arl R11-1 36 H NH Ar2 R11-1 2 H NH Arl R11-2 37 H NH Ar2 R11-2 3 H NH Arl R11-3 38 H NH Ar2 R11-3 4 H NH Arl R11-4 39 H NH Ar2 R11-4 H NH Arl R11-5 40 H NH Ar2 R11-5 6 H NH Arl R11-6 41 H NH Ar2 R11-6 7 H NH Arl R11-7 42 H NH Ar2 R11-7 8 H NH Arl R11-8 43 H NH Ar2 R11-8 9 H NH Arl R11-9 44 H NH Ar2 R11-9 H NH Arl R11-10 45 H NH Ar2 R11-10 11 H NH Arl R11-11 46 H NH Ar2 R11-11 12 H NH Arl R11-12 47 H NH Ar2 R11-12 13 H NH Arl R11-13 48 H NH Ar2 R11-13 14 H NH Arl R11-14 49 H NH Ar2 R11-14 H NH Arl R11-15 50 H NH Ar2 R11-15 16 H NH Arl R11-16 51 H NH Ar2 R11-16 17 H NH Arl R11-17 52 H NH Ar2 R11-17 18 H NH Arl R11-18 53 H NH Ar2 R11-18 19 H NH Arl R11-19 54 H NH Ar2 R11-19 H NH Arl R11-20 55 H NH Ar2 R11-20 21 H NH Arl R11-21 56 H NH Ar2 R11-21 22 H NH Arl R11-22 57 H NH Ar2 R11-22 23 H NH Arl R11-23 58 H NH Ar2 R11-23 24 H NH Arl R11-24 59 H NH Ar2 R11-24 H NH Arl R11-25 60 H NH Ar2 R11-25 26 H NH Arl R11-26 61 H NH Ar2 R11-26 27 H NH Arl R11-27 62 H NH Ar2 R11-27 28 H NH Arl R11-28 63 H NH Ar2 R11-28 29 H NH Arl R11-29 64 H NH Ar2 R11-29 H NH Arl A11-la 65 H NH Ar2 A11-la
31 H NH Arl A11-lb 66 H NH Ar2 A11-lb
32 H NH Arl A11-2a 67 H NH Ar2 A11-2a
33 H NH Arl A11-2b 68 H NH Ar2 A11-2b
34 H NH Arl A11-3a 69 H NH Ar2 A11-3a H NH Arl A11-3b 70 H NH Ar2 A11-3b Line R Q Ar D Line R Q Ar D
71 H NH Ar3 R11-1 110 H NH AO R11-5 72 H NH Ar3 R11-2 111 H NH AO R11-6 73 H NH Ar3 R11-3 112 H NH Art R11-7 74 H NH Ar3 R11-4 113 H NH Art R11-8 75 H NH Ar3 R11-5 114 H NH AO R11-9 76 H NH Ar3 R11-6 115 H NH Art R11-10 77 H NH Ar3 R11-7 116 H NH Art R11-11 78 H NH Ar3 R11-8 117 H NH Art R11-12 79 H NH Ar3 R11-9 118 H NH Art R11-13 80 H NH Ar3 R11-10 119 H NH Art R11-14 81 H NH Ar3 R11-11 120 H NH Art R11-15 82 H NH Ar3 R11-12 121 H NH Art R11-16 83 H NH Ar3 R11-13 122 H NH Art R11-17 84 H NH Ar3 R11-14 123 H NH Art R11-18 85 H NH Ar3 R11-15 124 H NH Art R11-19 86 H NH Ar3 R11-16 125 H NH Art R11-20 87 H NH Ar3 R11-17 126 H NH Art R11-21 88 H NH Ar3 R11-18 127 H NH Art R11-22 89 H NH Ar3 R11-19 128 H NH Art R11-23 90 H NH Ar3 R11-20 129 H NH Art R11-24 91 H NH Ar3 R11-21 130 H NH Art R11-25 92 H NH Ar3 R11-22 131 H NH Art R11-26 93 H NH Ar3 R11-23 132 H NH Art R11-27 94 H NH Ar3 R11-24 133 H NH Art R11-28 95 H NH Ar3 R11-25 134 H NH Art R11-29 96 H NH Ar3 R11-26 135 H NH Art A11-la 97 H NH Ar3 R11-27 136 H NH AO A11-lb 98 H NH Ar3 R11-28 137 H NH Art A11-2a 99 H NH Ar3 R11-29 138 H NH Art A11-2b 100 H NH Ar3 A11-la 139 H NH AO A11-3a 101 H NH Ar3 A11-lb 140 H NH AO A11-3b 102 H NH Ar3 A11-2a 141 H NH Ar5 R11-1 103 H NH Ar3 A11-2b 142 H NH Ar5 R11-2 104 H NH Ar3 A11-3a 143 H NH Ar5 R11-3 105 H NH AO A11-3b 144 H NH Ar5 R11-4 106 H NH Art R11-1 145 H NH Ar5 R11-5 107 H NH Art R11-2 146 H NH Ar5 R11-6 108 H NH Art R11-3 147 H NH Ar5 R11-7 109 H NH Art R11-4 148 H NH Ar5 R11-8 Line R Q Ar D Line R Q Ar D
149 H NH Ar5 R11-9 188 H NH Ar6 R11-13 150 H NH Ar5 R11-10 189 H NH Ar6 R11-14 151 H NH Ar5 R11-11 190 H NH Ar6 R11-15 152 H NH Ar5 R11-12 191 H NH Ar6 R11-16 153 H NH Ar5 R11-13 192 H NH Ar6 R11-17 154 H NH Ar5 R11-14 193 H NH Ar6 R11-18 155 H NH Ar5 R11-15 194 H NH Ar6 R11-19 156 H NH Ar5 R11-16 195 H NH Ar6 R11-20 157 H NH Ar5 R11-17 196 H NH Ar6 R11-21 158 H NH Ar5 R11-18 197 H NH Ar6 R11-22 159 H NH Ar5 R11-19 198 H NH Ar6 R11-23 160 H NH Ar5 R11-20 199 H NH Ar6 R11-24 161 H NH Ar5 R11-21 200 H NH Ar6 R11-25 162 H NH Ar5 R11-22 201 H NH Ar6 R11-26 163 H NH Ar5 R11-23 202 H NH Ar6 R11-27 164 H NH Ar5 R11-24 203 H NH Ar6 R11-28 165 H NH Ar5 R11-25 204 H NH Ar6 R11-29 166 H NH Ar5 R11-26 205 H NH Ar6 A11-la 167 H NH Ar5 R11-27 206 H NH Ar6 A11-1b 168 H NH Ar5 R11-28 207 H NH Ar6 A11-2a 169 H NH Ar5 R11-29 208 H NH Ar6 A11-2b 170 H NH Ar5 A11-la 209 H NH Ar6 A11-3a 171 H NH Ar5 A11-lb 210 H NH Ar6 A11-3b 172 H NH Ar5 A11-2a 211 H NH Ar7 R11-1 173 H NH Ar5 A11-2b 212 H NH Ar7 R11-2 174 H NH Ar5 A11-3a 213 H NH Ar7 R11-3 175 H NH Ar5 A11-3b 214 H NH AC R11-4 176 H NH Ar6 R11-1 215 H NH Ar7 R11-5 177 H NH Ar6 R11-2 216 H NH Ar7 R11-6 178 H NH Ar6 R11-3 217 H NH AC R11-7 179 H NH Ar6 R11-4 218 H NH AC R11-8 180 H NH Ar6 R11-5 219 H NH AC R11-9 181 H NH Ar6 R11-6 220 H NH Ar7 R11-10 182 H NH Ar6 R11-7 221 H NH AC R11-11 183 H NH Ar6 R11-8 222 H NH AC R11-12 184 H NH Ar6 R11-9 223 H NH Ar7 R11-13 185 H NH Ar6 R11-10 224 H NH Ar7 R11-14 186 H NH Ar6 R11-11 225 H NH Ar7 R11-15 187 H NH Ar6 R11-12 226 H NH Ar7 R11-16 Line R Q Ar D Line R Q Ar D
227 H NH AC R11-17 266 H NH Ar8 R11-21 228 H NH AC R11-18 267 H NH Ar8 R11-22 229 H NH Ar7 R11-19 268 H NH Ar8 R11-23 230 H NH Ar7 R11-20 269 H NH Ar8 R11-24 231 H NH AC R11-21 270 H NH Ar8 R11-25 232 H NH Ar7 R11-22 271 H NH Ar8 R11-26 233 H NH Ar7 R11-23 272 H NH Ar8 R11-27 234 H NH Ar7 R11-24 273 H NH Ar8 R11-28 235 H NH Ar7 R11-25 274 H NH Ar8 R11-29 236 H NH Ar7 R11-26 275 H NH Ar8 A11-la 237 H NH Ar7 R11-27 276 H NH Ar8 A11-1b 238 H NH Ar7 R11-28 277 H NH Ar8 A11-2a 239 H NH Ar7 R11-29 278 H NH Ar8 A11-2b 240 H NH Ar7 A11-la 279 H NH Ar8 A11-3a 241 H NH Ar7 A11-lb 280 H NH Ar8 A11-3b 242 H NH Ar7 A11-2a 281 H NH Ar9 R11-1 243 H NH Ar7 A11-2b 282 H NH Ar9 R11-2 244 H NH Ar7 A11-3a 283 H NH Ar9 R11-3 245 H NH Ar7 A11-3b 284 H NH Ar9 R11-4 246 H NH Ar8 R11-1 285 H NH Ar9 R11-5 247 H NH Ar8 R11-2 286 H NH Ar9 R11-6 248 H NH Ar8 R11-3 287 H NH Ar9 R11-7 249 H NH Ar8 R11-4 288 H NH Ar9 R11-8 250 H NH Ar8 R11-5 289 H NH Ar9 R11-9 251 H NH Ar8 R11-6 290 H NH Ar9 R11-10 252 H NH Ar8 R11-7 291 H NH Ar9 R11-11 253 H NH Ar8 R11-8 292 H NH Ar9 R11-12 254 H NH Ar8 R11-9 293 H NH Ar9 R11-13 255 H NH Ar8 R11-10 294 H NH Ar9 R11-14 256 H NH Ar8 R11-11 295 H NH Ar9 R11-15 257 H NH Ar8 R11-12 296 H NH Ar9 R11-16 258 H NH Ar8 R11-13 297 H NH Ar9 R11-17 259 H NH Ar8 R11-14 298 H NH Ar9 R11-18 260 H NH Ar8 R11-15 299 H NH Ar9 R11-19 261 H NH Ar8 R11-16 300 H NH Ar9 R11-20 262 H NH Ar8 R11-17 301 H NH Ar9 R11-21 263 H NH Ar8 R11-18 302 H NH Ar9 R11-22 264 H NH Ar8 R11-19 303 H NH Ar9 R11-23 265 H NH Ar8 R11-20 304 H NH Ar9 R11-24 Line R Q Ar D Line R Q Ar D
305 H NH Ar9 R11-25 344 H NH Arl R11-29 306 H NH Ar9 R11-26 345 H NH Arl A11-la 307 H NH Ar9 R11-27 346 H NH Arlo A11-lb 308 H NH Ar9 R11-28 347 H NH Arlo A11-2a 309 H NH Ar9 R11-29 348 H NH Arl A11-2b 310 H NH Ar9 A11-la 349 H NH Arlo A11-3a 311 H NH Ar9 A11-lb 350 H NH Arlo A11-3b 312 H NH Ar9 A11-2a 351 H NH Aril R11-1 313 H NH Ar9 A11-2b 352 H NH Aril R11-2 314 H NH Ar9 A11-3a 353 H NH Aril R11-3 315 H NH Ar9 A11-3b 354 H NH Aril R11-4 316 H NH Arlo R11-1 355 H NH Aril R11-5 317 H NH Arlo R11-2 356 H NH Aril R11-6 318 H NH Arlo R11-3 357 H NH Aril R11-7 319 H NH Arlo R11-4 358 H NH Aril R11-8 320 H NH Arlo R11-5 359 H NH Aril R11-9 321 H NH Arlo R11-6 360 H NH Aril R11-10 322 H NH Arlo R11-7 361 H NH Aril R11-11 323 H NH Arlo R11-8 362 H NH Aril R11-12 324 H NH Arlo R11-9 363 H NH Aril R11-13 325 H NH Arlo R11-10 364 H NH Aril R11-14 326 H NH Arlo R11-11 365 H NH Aril R11-15 327 H NH Arlo R11-12 366 H NH Aril R11-16 328 H NH Arlo R11-13 367 H NH Aril R11-17 329 H NH Arlo R11-14 368 H NH Aril R11-18 330 H NH Arlo R11-15 369 H NH Aril R11-19 331 H NH Arl R11-16 370 H NH Aril R11-20 332 H NH Arlo R11-17 371 H NH Aril R11-21 333 H NH Arlo R11-18 372 H NH Aril R11-22 334 H NH Arl R11-19 373 H NH Aril R11-23 335 H NH Arl R11-20 374 H NH Aril R11-24 336 H NH Arl R11-21 375 H NH Aril R11-25 337 H NH Arlo R11-22 376 H NH Aril R11-26 338 H NH Arl R11-23 377 H NH Aril R11-27 339 H NH Arl R11-24 378 H NH Aril R11-28 340 H NH Arlo R11-25 379 H NH Aril R11-29 341 H NH Arlo R11-26 380 H NH Aril A11-la 342 H NH Arlo R11-27 381 H NH Aril A11-lb 343 H NH Arlo R11-28 382 H NH Aril A11-2a Line R Q Ar D Line R Q Ar D
383 H NH Aril A11-2b 422 H NCH3 Arl R11-2 384 H NH Aril A11-3a 423 H NCH3 Arl R11-3 385 H NH Aril A11-3b 424 H NCH3 Arl R11-4 386 H NH Ar12 R11-1 425 H NCH3 Arl R11-5 387 H NH Ar12 R11-2 426 H NCH3 Arl R11-6 388 H NH Ar12 R11-3 427 H NCH3 Arl R11-7 389 H NH Ar12 R11-4 428 H NCH3 Arl R11-8 390 H NH Ar12 R11-5 429 H NCH3 Arl R11-9 391 H NH Ar12 R11-6 430 H NCH3 Arl R11-10 392 H NH Ar12 R11-7 431 H NCH3 Arl R11-11 393 H NH Ar12 R11-8 432 H NCH3 Arl R11-12 394 H NH Ar12 R11-9 433 H NCH3 Arl R11-13 395 H NH Ar12 R11-10 434 H NCH3 Arl R11-14 396 H NH Ar12 R11-11 435 H NCH3 Arl R11-15 397 H NH Ar12 R11-12 436 H NCH3 Arl R11-16 398 H NH Ar12 R11-13 437 H NCH3 Arl R11-17 399 H NH Ar12 R11-14 438 H NCH3 Arl R11-18 400 H NH Ar12 R11-15 439 H NCH3 Arl R11-19 401 H NH Ar12 R11-16 440 H NCH3 Arl R11-20 402 H NH Ar12 R11-17 441 H NCH3 Arl R11-21 403 H NH Ar12 R11-18 442 H NCH3 Arl R11-22 404 H NH Ar12 R11-19 443 H NCH3 Arl R11-23 405 H NH Ar12 R11-20 444 H NCH3 Arl R11-24 406 H NH Ar12 R11-21 445 H NCH3 Arl R11-25 407 H NH Ar12 R11-22 446 H NCH3 Arl R11-26 408 H NH Ar12 R11-23 447 H NCH3 Arl R11-27 409 H NH Ar12 R11-24 448 H NCH3 Arl R11-28 410 H NH Ar12 R11-25 449 H NCH3 Arl R11-29 411 H NH Ar12 R11-26 450 H NCH3 Arl A11-la 412 H NH Ar12 R11-27 451 H NCH3 Arl A11-lb 413 H NH Ar12 R11-28 452 H NCH3 Arl A11-2a 414 H NH Ar12 R11-29 453 H NCH3 Arl A11-2b 415 H NH Ar12 A11-la 454 H NCH3 Arl A11-3a 416 H NH Ar12 A11-lb 455 H NCH3 Arl A11-3b 417 H NH Ar12 A11-2a 456 H NCH3 Ar2 R11-1 418 H NH Ar12 A11-2b 457 H NCH3 Ar2 R11-2 419 H NH Ar12 A11-3a 458 H NCH3 Ar2 R11-3 420 H NH Ar12 A11-3b 459 H NCH3 Ar2 R11-4 421 H NCH3 Arl R11-1 460 H NCH3 Ar2 R11-5 Line R Q Ar D Line R Q Ar D
461 H NCH3 Ar2 R11-6 500 H NCH3 Ar3 R11-10 462 H NCH3 Ar2 R11-7 501 H NCH3 Ar3 R11-11 463 H NCH3 Ar2 R11-8 502 H NCH3 Ar3 R11-12 464 H NCH3 Ar2 R11-9 503 H NCH3 Ar3 R11-13 465 H NCH3 Ar2 R11-10 504 H NCH3 Ar3 R11-14 466 H NCH3 Ar2 R11-11 505 H NCH3 Ar3 R11-15 467 H NCH3 Ar2 R11-12 506 H NCH3 Ar3 R11-16 468 H NCH3 Ar2 R11-13 507 H NCH3 Ar3 R11-17 469 H NCH3 Ar2 R11-14 508 H NCH3 Ar3 R11-18 470 H NCH3 Ar2 R11-15 509 H NCH3 Ar3 R11-19 471 H NCH3 Ar2 R11-16 510 H NCH3 Ar3 R11-20 472 H NCH3 Ar2 R11-17 511 H NCH3 Ar3 R11-21 473 H NCH3 Ar2 R11-18 512 H NCH3 Ar3 R11-22 474 H NCH3 Ar2 R11-19 513 H NCH3 Ar3 R11-23 475 H NCH3 Ar2 R11-20 514 H NCH3 Ar3 R11-24 476 H NCH3 Ar2 R11-21 515 H NCH3 Ar3 R11-25 477 H NCH3 Ar2 R11-22 516 H NCH3 Ar3 R11-26 478 H NCH3 Ar2 R11-23 517 H NCH3 Ar3 R11-27 479 H NCH3 Ar2 R11-24 518 H NCH3 Ar3 R11-28 480 H NCH3 Ar2 R11-25 519 H NCH3 Ar3 R11-29 481 H NCH3 Ar2 R11-26 520 H NCH3 Ar3 A11-la 482 H NCH3 Ar2 R11-27 521 H NCH3 Ar3 A11-lb 483 H NCH3 Ar2 R11-28 522 H NCH3 Ar3 A11-2a 484 H NCH3 Ar2 R11-29 523 H NCH3 Ar3 A11-2b 485 H NCH3 Ar2 A11-la 524 H NCH3 Ar3 A11-3a 486 H NCH3 Ar2 A11-1b 525 H NCH3 Ar4 A11-3b 487 H NCH3 Ar2 A11-2a 526 H NCH3 Ar4 R11-1 488 H NCH3 Ar2 A11-2b 527 H NCH3 Ar4 R11-2 489 H NCH3 Ar2 A11-3a 528 H NCH3 Ar4 R11-3 490 H NCH3 Ar2 A11-3b 529 H NCH3 Ar4 R11-4 491 H NCH3 Ar3 R11-1 530 H NCH3 Ar4 R11-5 492 H NCH3 Ar3 R11-2 531 H NCH3 Ar4 R11-6 493 H NCH3 Ar3 R11-3 532 H NCH3 Ar4 R11-7 494 H NCH3 Ar3 R11-4 533 H NCH3 Ar4 R11-8 495 H NCH3 Ar3 R11-5 534 H NCH3 Ar4 R11-9 496 H NCH3 Ar3 R11-6 535 H NCH3 Ar4 R11-10 497 H NCH3 Ar3 R11-7 536 H NCH3 Ar4 R11-11 498 H NCH3 Ar3 R11-8 537 H NCH3 Ar4 R11-12 499 H NCH3 Ar3 R11-9 538 H NCH3 Ar4 R11-13 Line R Q Ar D Line R Q Ar D
539 H NCH3 AO R11-14 578 H NCH3 Ar5 R11-18 540 H NCH3 AO R11-15 579 H NCH3 Ar5 R11-19 541 H NCH3 Art R11-16 580 H NCH3 Ar5 R11-20 542 H NCH3 Art R11-17 581 H NCH3 Ar5 R11-21 543 H NCH3 AO R11-18 582 H NCH3 Ar5 R11-22 544 H NCH3 Art R11-19 583 H NCH3 Ar5 R11-23 545 H NCH3 Art R11-20 584 H NCH3 Ar5 R11-24 546 H NCH3 Art R11-21 585 H NCH3 Ar5 R11-25 547 H NCH3 Art R11-22 586 H NCH3 Ar5 R11-26 548 H NCH3 Art R11-23 587 H NCH3 Ar5 R11-27 549 H NCH3 Art R11-24 588 H NCH3 Ar5 R11-28 550 H NCH3 Art R11-25 589 H NCH3 Ar5 R11-29 551 H NCH3 Art R11-26 590 H NCH3 Ar5 A11-la 552 H NCH3 Art R11-27 591 H NCH3 Ar5 A11-lb 553 H NCH3 Art R11-28 592 H NCH3 Ar5 A11-2a 554 H NCH3 Art R11-29 593 H NCH3 Ar5 A11-2b 555 H NCH3 Art A11-la 594 H NCH3 Ar5 A11-3a 556 H NCH3 Art A11-1b 595 H NCH3 Ar5 A11-3b 557 H NCH3 Art A11-2a 596 H NCH3 Ar6 R11-1 558 H NCH3 Art A11-2b 597 H NCH3 Ar6 R11-2 559 H NCH3 Art A11-3a 598 H NCH3 Ar6 R11-3 560 H NCH3 Art A11-3b 599 H NCH3 Ar6 R11-4 561 H NCH3 Ar5 R11-1 600 H NCH3 Ar6 R11-5 562 H NCH3 Ar5 R11-2 601 H NCH3 Ar6 R11-6 563 H NCH3 Ar5 R11-3 602 H NCH3 Ar6 R11-7 564 H NCH3 Ar5 R11-4 603 H NCH3 Ar6 R11-8 565 H NCH3 Ar5 R11-5 604 H NCH3 Ar6 R11-9 566 H NCH3 Ar5 R11-6 605 H NCH3 Ar6 R11-10 567 H NCH3 Ar5 R11-7 606 H NCH3 Ar6 R11-11 568 H NCH3 Ar5 R11-8 607 H NCH3 Ar6 R11-12 569 H NCH3 Ar5 R11-9 608 H NCH3 Ar6 R11-13 570 H NCH3 Ar5 R11-10 609 H NCH3 Ar6 R11-14 571 H NCH3 Ar5 R11-11 610 H NCH3 Ar6 R11-15 572 H NCH3 Ar5 R11-12 611 H NCH3 Ar6 R11-16 573 H NCH3 Ar5 R11-13 612 H NCH3 Ar6 R11-17 574 H NCH3 Ar5 R11-14 613 H NCH3 Ar6 R11-18 575 H NCH3 Ar5 R11-15 614 H NCH3 Ar6 R11-19 576 H NCH3 Ar5 R11-16 615 H NCH3 Ar6 R11-20 577 H NCH3 Ar5 R11-17 616 H NCH3 Ar6 R11-21 Line R Q Ar D Line R Q Ar D
617 H NCH3 Ar6 R11-22 656 H NCH3 AC R11-26 618 H NCH3 Ar6 R11-23 657 H NCH3 AC R11-27 619 H NCH3 Ar6 R11-24 658 H NCH3 Ar7 R11-28 620 H NCH3 Ar6 R11-25 659 H NCH3 Ar7 R11-29 621 H NCH3 Ar6 R11-26 660 H NCH3 AC A11-la 622 H NCH3 Ar6 R11-27 661 H NCH3 Ar7 A11-lb 623 H NCH3 Ar6 R11-28 662 H NCH3 Ar7 A11-2a 624 H NCH3 Ar6 R11-29 663 H NCH3 Ar7 A11-2b 625 H NCH3 Ar6 A11-la 664 H NCH3 Ar7 A11-3a 626 H NCH3 Ar6 A11-lb 665 H NCH3 Ar7 A11-3b 627 H NCH3 Ar6 A11-2a 666 H NCH3 Ar8 R11-1 628 H NCH3 Ar6 A11-2b 667 H NCH3 Ar8 R11-2 629 H NCH3 Ar6 A11-3a 668 H NCH3 Ar8 R11-3 630 H NCH3 Ar6 A11-3b 669 H NCH3 Ar8 R11-4 631 H NCH3 Ar7 R11-1 670 H NCH3 Ar8 R11-5 632 H NCH3 Ar7 R11-2 671 H NCH3 Ar8 R11-6 633 H NCH3 Ar7 R11-3 672 H NCH3 Ar8 R11-7 634 H NCH3 Ar7 R11-4 673 H NCH3 Ar8 R11-8 635 H NCH3 Ar7 R11-5 674 H NCH3 Ar8 R11-9 636 H NCH3 Ar7 R11-6 675 H NCH3 Ar8 R11-10 637 H NCH3 Ar7 R11-7 676 H NCH3 Ar8 R11-11 638 H NCH3 Ar7 R11-8 677 H NCH3 Ar8 R11-12 639 H NCH3 Ar7 R11-9 678 H NCH3 Ar8 R11-13 640 H NCH3 Ar7 R11-10 679 H NCH3 Ar8 R11-14 641 H NCH3 Ar7 R11-11 680 H NCH3 Ar8 R11-15 642 H NCH3 Ar7 R11-12 681 H NCH3 Ar8 R11-16 644 H NCH3 Ar7 R11-14 683 H NCH3 Ar8 R11-18 645 H NCH3 Ar7 R11-15 684 H NCH3 Ar8 R11-19 649 H NCH3 Ar7 R11-19 688 H NCH3 Ar8 R11-23 652 H NCH3 Ar7 R11-22 691 H NCH3 Ar8 R11-26 653 H NCH3 Ar7 R11-23 692 H NCH3 Ar8 R11-27 654 H NCH3 Ar7 R11-24 693 H NCH3 Ar8 R11-28 655 H NCH3 Ar7 R11-25 694 H NCH3 Ar8 R11-29 Line R Q Ar D Line R Q Ar D
695 H NCH3 Ar8 A11-la 734 H NCH3 Ar9 A11-3a 696 H NCH3 Ar8 A11-1b 735 H NCH3 Ar9 A11-3b 697 H NCH3 Ar8 A11-2a 736 H NCH3 Arlo R11-1 698 H NCH3 Ar8 A11-2b 737 H NCH3 Arlo R11-2 699 H NCH3 Ar8 A11-3a 738 H NCH3 Arl R11-3 700 H NCH3 Ar8 A11-3b 739 H NCH3 Arlo R11-4 701 H NCH3 Ar9 R11-1 740 H NCH3 Arlo R11-5 702 H NCH3 Ar9 R11-2 741 H NCH3 Arlo R11-6 703 H NCH3 Ar9 R11-3 742 H NCH3 Arlo R11-7 704 H NCH3 Ar9 R11-4 743 H NCH3 Arlo R11-8 705 H NCH3 Ar9 R11-5 744 H NCH3 Arlo R11-9 706 H NCH3 Ar9 R11-6 745 H NCH3 Arlo R11-10 707 H NCH3 Ar9 R11-7 746 H NCH3 Arlo R11-11 708 H NCH3 Ar9 R11-8 747 H NCH3 Arlo R11-12 709 H NCH3 Ar9 R11-9 748 H NCH3 Arlo R11-13 710 H NCH3 Ar9 R11-10 749 H NCH3 Arlo R11-14 711 H NCH3 Ar9 R11-11 750 H NCH3 Arlo R11-15 712 H NCH3 Ar9 R11-12 751 H NCH3 Arlo R11-16 713 H NCH3 Ar9 R11-13 752 H NCH3 Arlo R11-17 714 H NCH3 Ar9 R11-14 753 H NCH3 Arlo R11-18 715 H NCH3 Ar9 R11-15 754 H NCH3 Arlo R11-19 716 H NCH3 Ar9 R11-16 755 H NCH3 Arlo R11-20 717 H NCH3 Ar9 R11-17 756 H NCH3 Arlo R11-21 718 H NCH3 Ar9 R11-18 757 H NCH3 Arlo R11-22 719 H NCH3 Ar9 R11-19 758 H NCH3 Arlo R11-23 720 H NCH3 Ar9 R11-20 759 H NCH3 Arlo R11-24 721 H NCH3 Ar9 R11-21 760 H NCH3 Arl R11-25 722 H NCH3 Ar9 R11-22 761 H NCH3 Arlo R11-26 723 H NCH3 Ar9 R11-23 762 H NCH3 Arlo R11-27 724 H NCH3 Ar9 R11-24 763 H NCH3 Arl R11-28 725 H NCH3 Ar9 R11-25 764 H NCH3 Arl R11-29 726 H NCH3 Ar9 R11-26 765 H NCH3 Arl A11-la 727 H NCH3 Ar9 R11-27 766 H NCH3 Arlo A11-lb 728 H NCH3 Ar9 R11-28 767 H NCH3 Arl A11-2a 729 H NCH3 Ar9 R11-29 768 H NCH3 Arl A11-2b 730 H NCH3 Ar9 A11-la 769 H NCH3 Arlo A11-3a 731 H NCH3 Ar9 A11-lb 770 H NCH3 Arlo A11-3b 732 H NCH3 Ar9 A11-2a 771 H NCH3 Aril R11-1 733 H NCH3 Ar9 A11-2b 772 H NCH3 Aril R11-2 Line R Q Ar D Line R Q Ar D
773 H NCH3 Aril R11-3 812 H NCH3 Ar12 R11-7 774 H NCH3 Aril R11-4 813 H NCH3 Ar12 R11-8 775 H NCH3 Aril R11-5 814 H NCH3 Ar12 R11-9 776 H NCH3 Aril R11-6 815 H NCH3 Ar12 R11-10 777 H NCH3 Aril R11-7 816 H NCH3 Ar12 R11-11 778 H NCH3 Aril R11-8 817 H NCH3 Ar12 R11-12 779 H NCH3 Aril R11-9 818 H NCH3 Ar12 R11-13 780 H NCH3 Aril R11-10 819 H NCH3 Ar12 R11-14 781 H NCH3 Aril R11-11 820 H NCH3 Ar12 R11-15 782 H NCH3 Aril R11-12 821 H NCH3 Ar12 R11-16 783 H NCH3 Aril R11-13 822 H NCH3 Ar12 R11-17 784 H NCH3 Aril R11-14 823 H NCH3 Ar12 R11-18 785 H NCH3 Aril R11-15 824 H NCH3 Ar12 R11-19 786 H NCH3 Aril R11-16 825 H NCH3 Ar12 R11-20 787 H NCH3 Aril R11-17 826 H NCH3 Ar12 R11-21 788 H NCH3 Aril R11-18 827 H NCH3 Ar12 R11-22 789 H NCH3 Aril R11-19 828 H NCH3 Ar12 R11-23 790 H NCH3 Aril R11-20 829 H NCH3 Ar12 R11-24 791 H NCH3 Aril R11-21 830 H NCH3 Ar12 R11-25 792 H NCH3 Aril R11-22 831 H NCH3 Ar12 R11-26 793 H NCH3 Aril R11-23 832 H NCH3 Ar12 R11-27 794 H NCH3 Aril R11-24 833 H NCH3 Ar12 R11-28 795 H NCH3 Aril R11-25 834 H NCH3 Ar12 R11-29 796 H NCH3 Aril R11-26 835 H NCH3 Ar12 A11-la 797 H NCH3 Aril R11-27 836 H NCH3 Ar12 A11-lb 798 H NCH3 Aril R11-28 837 H NCH3 Ar12 A11-2a 799 H NCH3 Aril R11-29 838 H NCH3 Ar12 A11-2b 800 H NCH3 Aril A11-la 839 H NCH3 Ar12 A11-3a 801 H NCH3 Aril A11-lb 840 H NCH3 Ar12 A11-3b 802 H NCH3 Aril A11-2a 841 H 0 Arl R11-1 803 H NCH3 Aril A11-2b 842 H 0 Arl R11-2 804 H NCH3 Aril A11-3a 843 H 0 Arl R11-3 805 H NCH3 Aril A11-3b 844 H 0 Arl R11-4 806 H NCH3 Ar12 R11-1 845 H 0 Arl R11-5 807 H NCH3 Ar12 R11-2 846 H 0 Arl R11-6 808 H NCH3 Ar12 R11-3 847 H 0 Arl R11-7 809 H NCH3 Ar12 R11-4 848 H 0 Arl R11-8 810 H NCH3 Ar12 R11-5 849 H 0 Arl R11-9 811 H NCH3 Ar12 R11-6 850 H 0 Arl R11-10 Line R Q Ar D Line R Q Ar D
851 H 0 Arl R11-11 890 H 0 Ar2 R11-15 852 H 0 Arl R11-12 891 H 0 Ar2 R11-16 853 H 0 Arl R11-13 892 H 0 Ar2 R11-17 854 H 0 Arl R11-14 893 H 0 Ar2 R11-18 855 H 0 Arl R11-15 894 H 0 Ar2 R11-19 856 H 0 Arl R11-16 895 H 0 Ar2 R11-20 857 H 0 Arl R11-17 896 H 0 Ar2 R11-21 858 H 0 Arl R11-18 897 H 0 Ar2 R11-22 859 H 0 Arl R11-19 898 H 0 Ar2 R11-23 860 H 0 Arl R11-20 899 H 0 Ar2 R11-24 861 H 0 Arl R11-21 900 H 0 Ar2 R11-25 862 H 0 Arl R11-22 901 H 0 Ar2 R11-26 863 H 0 Arl R11-23 902 H 0 Ar2 R11-27 864 H 0 Arl R11-24 903 H 0 Ar2 R11-28 865 H 0 Arl R11-25 904 H 0 Ar2 R11-29 866 H 0 Arl R11-26 905 H 0 Ar2 A11-la 867 H 0 Arl R11-27 906 H 0 Ar2 A11-lb 868 H 0 Arl R11-28 907 H 0 Ar2 A11-2a 869 H 0 Arl R11-29 908 H 0 Ar2 A11-2b 870 H 0 Arl A11-la 909 H 0 Ar2 A11-3a 871 H 0 Arl A11-1b 910 H 0 Ar2 A11-3b 872 H 0 Arl A11-2a 911 H 0 Ar3 R11-1 873 H 0 Arl A11-2b 912 H 0 Ar3 R11-2 874 H 0 Arl A11-3a 913 H 0 Ar3 R11-3 875 H 0 Arl A11-3b 914 H 0 Ar3 R11-4 876 H 0 Ar2 R11-1 915 H 0 Ar3 R11-5 877 H 0 Ar2 R11-2 916 H 0 Ar3 R11-6 878 H 0 Ar2 R11-3 917 H 0 Ar3 R11-7 879 H 0 Ar2 R11-4 918 H 0 Ar3 R11-8 880 H 0 Ar2 R11-5 919 H 0 Ar3 R11-9 881 H 0 Ar2 R11-6 920 H 0 Ar3 R11-10 882 H 0 Ar2 R11-7 921 H 0 Ar3 R11-11 883 H 0 Ar2 R11-8 922 H 0 Ar3 R11-12 884 H 0 Ar2 R11-9 923 H 0 Ar3 R11-13 885 H 0 Ar2 R11-10 924 H 0 Ar3 R11-14 886 H 0 Ar2 R11-11 925 H 0 Ar3 R11-15 887 H 0 Ar2 R11-12 926 H 0 Ar3 R11-16 888 H 0 Ar2 R11-13 927 H 0 Ar3 R11-17 889 H 0 Ar2 R11-14 928 H 0 Ar3 R11-18 Line R Q Ar D Line R Q Ar D
929 H 0 Ar3 R11-19 968 H 0 Ar4 R11-23 930 H 0 Ar3 R11-20 969 H 0 Ar4 R11-24 931 H 0 Ar3 R11-21 970 H 0 Ar4 R11-25 932 H 0 Ar3 R11-22 971 H 0 Ar4 R11-26 933 H 0 Ar3 R11-23 972 H 0 Ar4 R11-27 934 H 0 Ar3 R11-24 973 H 0 Ar4 R11-28 935 H 0 Ar3 R11-25 974 H 0 Ar4 R11-29 936 H 0 Ar3 R11-26 975 H 0 Ar4 A11-la 937 H 0 Ar3 R11-27 976 H 0 Ar4 A11-1b 938 H 0 Ar3 R11-28 977 H 0 Ar4 A11-2a 939 H 0 Ar3 R11-29 978 H 0 Ar4 A11-2b 940 H 0 Ar3 A11- 1 a 979 H 0 Ar4 A11-3a 941 H 0 Ar3 A11- 1 b 980 H 0 Ar4 A11-3b 942 H 0 Ar3 A11-2a 981 H 0 Ar5 R11-1 943 H 0 Ar3 A11-2b 982 H 0 Ar5 R11-2 944 H 0 Ar3 A11-3a 983 H 0 Ar5 R11-3 945 H 0 Art A11-3b 984 H 0 Ar5 R11-4 946 H 0 Art R11-1 985 H 0 Ar5 R11-5 947 H 0 Art R11-2 986 H 0 Ar5 R11-6 948 H 0 Art R11-3 987 H 0 Ar5 R11-7 949 H 0 Art R11-4 988 H 0 Ar5 R11-8 950 H 0 Art R11-5 989 H 0 Ar5 R11-9 951 H 0 Art R11-6 990 H 0 Ar5 R11-10 952 H 0 Art R11-7 991 H 0 Ar5 R11-11 953 H 0 Art R11-8 992 H 0 Ar5 R11-12 954 H 0 Art R11-9 993 H 0 Ar5 R11-13 955 H 0 AO R11-10 994 H 0 Ar5 R11-14 956 H 0 Art R11-11 995 H 0 Ar5 R11-15 957 H 0 Art R11-12 996 H 0 Ar5 R11-16 958 H 0 AO R11-13 997 H 0 Ar5 R11-17 959 H 0 AO R11-14 998 H 0 Ar5 R11-18 960 H 0 AO R11-15 999 H 0 Ar5 R11-19 961 H 0 Art R11-16 1000 H 0 Ar5 R11-20 962 H 0 AO R11-17 1001 H 0 Ar5 R11-21 963 H 0 AO R11-18 1002 H 0 Ar5 R11-22 964 H 0 Art R11-19 1003 H 0 Ar5 R11-23 965 H 0 Art R11-20 1004 H 0 Ar5 R11-24 966 H 0 Art R11-21 1005 H 0 Ar5 R11-25 967 H 0 Art R11-22 1006 H 0 Ar5 R11-26 Line R Q Ar D Line R Q Ar D
1007 H 0 Ar5 R11-27 1046 H 0 Ar6 A11-1b 1008 H 0 Ar5 R11-28 1047 H 0 Ar6 A11-2a 1009 H 0 Ar5 R11-29 1048 H 0 Ar6 A11-2b 1010 H 0 Ar5 A11-la 1049 H 0 Ar6 A11-3a 1011 H 0 Ar5 A11-lb 1050 H 0 Ar6 A11-3b 1012 H 0 Ar5 A11-2a 1051 H 0 Ar7 R11-1 1013 H 0 Ar5 A11-2b 1052 H 0 Ar7 R11-2 1014 H 0 Ar5 A11-3a 1053 H 0 Ar7 R11-3 1015 H 0 Ar5 A11-3b 1054 H 0 Ar7 R11-4 1016 H 0 Ar6 R11-1 1055 H 0 Ar7 R11-5 1017 H 0 Ar6 R11-2 1056 H 0 Ar7 R11-6 1018 H 0 Ar6 R11-3 1057 H 0 Ar7 R11-7 1019 H 0 Ar6 R11-4 1058 H 0 Ar7 R11-8 1020 H 0 Ar6 R11-5 1059 H 0 Ar7 R11-9 1021 H 0 Ar6 R11-6 1060 H 0 Ar7 R11-10 1022 H 0 Ar6 R11-7 1061 H 0 Ar7 R11-11 1023 H 0 Ar6 R11-8 1062 H 0 Ar7 R11-12 1024 H 0 Ar6 R11-9 1063 H 0 Ar7 R11-13 1025 H 0 Ar6 R11-10 1064 H 0 Ar7 R11-14 1026 H 0 Ar6 R11-11 1065 H 0 Ar7 R11-15 1027 H 0 Ar6 R11-12 1066 H 0 Ar7 R11-16 1028 H 0 Ar6 R11-13 1067 H 0 Ar7 R11-17 1029 H 0 Ar6 R11-14 1068 H 0 Ar7 R11-18 1030 H 0 Ar6 R11-15 1069 H 0 Ar7 R11-19 1031 H 0 Ar6 R11-16 1070 H 0 Ar7 R11-20 1032 H 0 Ar6 R11-17 1071 H 0 Ar7 R11-21 1033 H 0 Ar6 R11-18 1072 H 0 Ar7 R11-22 1034 H 0 Ar6 R11-19 1073 H 0 Ar7 R11-23 1035 H 0 Ar6 R11-20 1074 H 0 Ar7 R11-24 1036 H 0 Ar6 R11-21 1075 H 0 Ar7 R11-25 1037 H 0 Ar6 R11-22 1076 H 0 Ar7 R11-26 1038 H 0 Ar6 R11-23 1077 H 0 Ar7 R11-27 1039 H 0 Ar6 R11-24 1078 H 0 Ar7 R11-28 1040 H 0 Ar6 R11-25 1079 H 0 Ar7 R11-29 1041 H 0 Ar6 R11-26 1080 H 0 Ar7 A11-la 1042 H 0 Ar6 R11-27 1081 H 0 Ar7 A11-lb 1043 H 0 Ar6 R11-28 1082 H 0 Ar7 A11-2a 1044 H 0 Ar6 R11-29 1083 H 0 Ar7 A11-2b 1045 H 0 Ar6 A11- 1 a 1084 H 0 Ar7 A11-3a Line R Q Ar D Line R Q Ar D
1085 H 0 Ar7 A11-3b 1124 H 0 Ar9 R11-4 1086 H 0 Ar8 R11-1 1125 H 0 Ar9 R11-5 1087 H 0 Ar8 R11-2 1126 H 0 Ar9 R11-6 1088 H 0 Ar8 R11-3 1127 H 0 Ar9 R11-7 1089 H 0 Ar8 R11-4 1128 H 0 Ar9 R11-8 1090 H 0 Ar8 R11-5 1129 H 0 Ar9 R11-9 1091 H 0 Ar8 R11-6 1130 H 0 Ar9 R11-10 1092 H 0 Ar8 R11-7 1131 H 0 Ar9 R11-11 1093 H 0 Ar8 R11-8 1132 H 0 Ar9 R11-12 1094 H 0 Ar8 R11-9 1133 H 0 Ar9 R11-13 1095 H 0 Ar8 R11-10 1134 H 0 Ar9 R11-14 1096 H 0 Ar8 R11-11 1135 H 0 Ar9 R11-15 1097 H 0 Ar8 R11-12 1136 H 0 Ar9 R11-16 1098 H 0 Ar8 R11-13 1137 H 0 Ar9 R11-17 1099 H 0 Ar8 R11-14 1138 H 0 Ar9 R11-18 1100 H 0 Ar8 R11-15 1139 H 0 Ar9 R11-19 1101 H 0 Ar8 R11-16 1140 H 0 Ar9 R11-20 1102 H 0 Ar8 R11-17 1141 H 0 Ar9 R11-21 1103 H 0 Ar8 R11-18 1142 H 0 Ar9 R11-22 1104 H 0 Ar8 R11-19 1143 H 0 Ar9 R11-23 1105 H 0 Ar8 R11-20 1144 H 0 Ar9 R11-24 1106 H 0 Ar8 R11-21 1145 H 0 Ar9 R11-25 1107 H 0 Ar8 R11-22 1146 H 0 Ar9 R11-26 1108 H 0 Ar8 R11-23 1147 H 0 Ar9 R11-27 1109 H 0 Ar8 R11-24 1148 H 0 Ar9 R11-28 1110 H 0 Ar8 R11-25 1149 H 0 Ar9 R11-29 1111 H 0 Ar8 R11-26 1150 H 0 Ar9 A11-la 1112 H 0 Ar8 R11-27 1151 H 0 Ar9 A11-lb 1113 H 0 Ar8 R11-28 1152 H 0 Ar9 A11-2a 1114 H 0 Ar8 R11-29 1153 H 0 Ar9 A11-2b 1115 H 0 Ar8 A11-la 1154 H 0 Ar9 A11-3a 1116 H 0 Ar8 A11-lb 1155 H 0 Ar9 A11-3b 1117 H 0 Ar8 A11-2a 1156 H 0 Arlo R11-1 1118 H 0 Ar8 A11-2b 1157 H 0 Arl R11-2 1119 H 0 Ar8 A11-3a 1158 H 0 Arl R11-3 1120 H 0 Ar8 A11-3b 1159 H 0 Arlo R11-4 1121 H 0 Ar9 R11-1 1160 H 0 Arlo R11-5 1122 H 0 Ar9 R11-2 1161 H 0 Arlo R11-6 1123 H 0 Ar9 R11-3 1162 H 0 Arlo R11-7 Line R Q Ar D Line R Q Ar D
1163 H 0 Arl R11-8 1202 H 0 Aril R11-12 1164 H 0 Arl R11-9 1203 H 0 Aril R11-13 1165 H 0 Arlo R11-10 1204 H 0 Aril R11-14 1166 H 0 Arlo R11-11 1205 H 0 Aril R11-15 1167 H 0 Arl R11-12 1206 H 0 Aril R11-16 1168 H 0 Arlo R11-13 1207 H 0 Aril R11-17 1169 H 0 Arlo R11-14 1208 H 0 Aril R11-18 1170 H 0 Arlo R11-15 1209 H 0 Aril R11-19 1171 H 0 Arlo R11-16 1210 H 0 Aril R11-20 1172 H 0 Arlo R11-17 1211 H 0 Aril R11-21 1173 H 0 Arlo R11-18 1212 H 0 Aril R11-22 1174 H 0 Arlo R11-19 1213 H 0 Aril R11-23 1175 H 0 Arlo R11-20 1214 H 0 Aril R11-24 1176 H 0 Arlo R11-21 1215 H 0 Aril R11-25 1177 H 0 Arlo R11-22 1216 H 0 Aril R11-26 1178 H 0 Arlo R11-23 1217 H 0 Aril R11-27 1179 H 0 Arlo R11-24 1218 H 0 Aril R11-28 1180 H 0 Arlo R11-25 1219 H 0 Aril R11-29 1181 H 0 Arlo R11-26 1220 H 0 Aril A11-la 1182 H 0 Arlo R11-27 1221 H 0 Aril A11-lb 1183 H 0 Arlo R11-28 1222 H 0 Aril A11-2a 1184 H 0 Arlo R11-29 1223 H 0 Aril A11-2b 1185 H 0 Arlo A11-la 1224 H 0 Aril A11-3a 1186 H 0 Arlo A11-lb 1225 H 0 Aril A11-3b 1187 H 0 Arlo A11-2a 1226 H 0 Ar12 R11-1 1188 H 0 Arlo A11-2b 1227 H 0 Ar12 R11-2 1189 H 0 Arl A11-3a 1228 H 0 Ar12 R11-3 1190 H 0 Arlo A11-3b 1229 H 0 Ar12 R11-4 1191 H 0 Aril R11-1 1230 H 0 Ar12 R11-5 1192 H 0 Aril R11-2 1231 H 0 Ar12 R11-6 1193 H 0 Aril R11-3 1232 H 0 Ar12 R11-7 1194 H 0 Aril R11-4 1233 H 0 Ar12 R11-8 1195 H 0 Aril R11-5 1234 H 0 Ar12 R11-9 1196 H 0 Aril R11-6 1235 H 0 Ar12 R11-10 1197 H 0 Aril R11-7 1236 H 0 Ar12 R11-11 1198 H 0 Aril R11-8 1237 H 0 Ar12 R11-12 1199 H 0 Aril R11-9 1238 H 0 Ar12 R11-13 1200 H 0 Aril R11-10 1239 H 0 Ar12 R11-14 1201 H 0 Aril R11-11 1240 H 0 Ar12 R11-15 Line R Q Ar D Line R Q Ar D
1241 H 0 Ar12 R11-16 1280 CH3 NH Arl R11-20 1242 H 0 Ar12 R11-17 1281 CH3 NH Arl R11-21 1243 H 0 Ar12 R11-18 1282 CH3 NH Arl R11-22 1244 H 0 Ar12 R11-19 1283 CH3 NH Arl R11-23 1245 H 0 Ar12 R11-20 1284 CH3 NH Arl R11-24 1246 H 0 Ar12 R11-21 1285 CH3 NH Arl R11-25 1247 H 0 Ar12 R11-22 1286 CH3 NH Arl R11-26 1248 H 0 Ar12 R11-23 1287 CH3 NH Arl R11-27 1249 H 0 Ar12 R11-24 1288 CH3 NH Arl R11-28 1250 H 0 Ar12 R11-25 1289 CH3 NH Arl R11-29 1251 H 0 Ar12 R11-26 1290 CH3 NH Arl A11-la 1252 H 0 Ar12 R11-27 1291 CH3 NH Arl A11-lb 1253 H 0 Ar12 R11-28 1292 CH3 NH Arl A11-2a 1254 H 0 Ar12 R11-29 1293 CH3 NH Arl A11-2b 1255 H 0 Ar12 A11-la 1294 CH3 NH Arl A11-3a 1256 H 0 Ar12 A11-lb 1295 CH3 NH Arl A11-3b 1257 H 0 Ar12 A11-2a 1296 CH3 NH Ar2 R11-1 1258 H 0 Ar12 A11-2b 1297 CH3 NH Ar2 R11-2 1259 H 0 Ar12 A11-3a 1298 CH3 NH Ar2 R11-3 1260 H 0 Ar12 A11-3b 1299 CH3 NH Ar2 R11-4 1261 CH3 NH Arl R11-1 1300 CH3 NH Ar2 R11-5 1262 CH3 NH Arl R11-2 1301 CH3 NH Ar2 R11-6 1263 CH3 NH Arl R11-3 1302 CH3 NH Ar2 R11-7 1264 CH3 NH Arl R11-4 1303 CH3 NH Ar2 R11-8 1265 CH3 NH Arl R11-5 1304 CH3 NH Ar2 R11-9 1266 CH3 NH Arl R11-6 1305 CH3 NH Ar2 R11-10 1267 CH3 NH Arl R11-7 1306 CH3 NH Ar2 R11-11 1268 CH3 NH Arl R11-8 1307 CH3 NH Ar2 R11-12 1269 CH3 NH Arl R11-9 1308 CH3 NH Ar2 R11-13 1270 CH3 NH Arl R11-10 1309 CH3 NH Ar2 R11-14 1271 CH3 NH Arl R11-11 1310 CH3 NH Ar2 R11-15 1272 CH3 NH Arl R11-12 1311 CH3 NH Ar2 R11-16 1273 CH3 NH Arl R11-13 1312 CH3 NH Ar2 R11-17 1274 CH3 NH Arl R11-14 1313 CH3 NH Ar2 R11-18 1275 CH3 NH Arl R11-15 1314 CH3 NH Ar2 R11-19 1276 CH3 NH Arl R11-16 1315 CH3 NH Ar2 R11-20 1277 CH3 NH Arl R11-17 1316 CH3 NH Ar2 R11-21 1278 CH3 NH Arl R11-18 1317 CH3 NH Ar2 R11-22 1279 CH3 NH Arl R11-19 1318 CH3 NH Ar2 R11-23 Line R Q Ar D Line R Q Ar D
1319 CH3 NH Ar2 R11-24 1358 CH3 NH Ar3 R11-28 1320 CH3 NH Ar2 R11-25 1359 CH3 NH Ar3 R11-29 1321 CH3 NH Ar2 R11-26 1360 CH3 NH Ar3 A11-la 1322 CH3 NH Ar2 R11-27 1361 CH3 NH Ar3 A11-lb 1323 CH3 NH Ar2 R11-28 1362 CH3 NH Ar3 A11-2a 1324 CH3 NH Ar2 R11-29 1363 CH3 NH Ar3 A11-2b 1325 CH3 NH Ar2 A11-la 1364 CH3 NH Ar3 A11-3a 1326 CH3 NH Ar2 A11-lb 1365 CH3 NH Art A11-3b 1327 CH3 NH Ar2 A11-2a 1366 CH3 NH Art R11-1 1328 CH3 NH Ar2 A11-2b 1367 CH3 NH Art R11-2 1329 CH3 NH Ar2 A11-3a 1368 CH3 NH Art R11-3 1330 CH3 NH Ar2 A11-3b 1369 CH3 NH Art R11-4 1331 CH3 NH Ar3 R11-1 1370 CH3 NH Art R11-5 1332 CH3 NH Ar3 R11-2 1371 CH3 NH Art R11-6 1333 CH3 NH Ar3 R11-3 1372 CH3 NH Art R11-7 1334 CH3 NH Ar3 R11-4 1373 CH3 NH Art R11-8 1335 CH3 NH Ar3 R11-5 1374 CH3 NH Art R11-9 1336 CH3 NH Ar3 R11-6 1375 CH3 NH Art R11-10 1337 CH3 NH Ar3 R11-7 1376 CH3 NH Art R11-11 1338 CH3 NH Ar3 R11-8 1377 CH3 NH Art R11-12 1339 CH3 NH Ar3 R11-9 1378 CH3 NH Art R11-13 1340 CH3 NH Ar3 R11-10 1379 CH3 NH Art R11-14 1341 CH3 NH Ar3 R11-11 1380 CH3 NH Art R11-15 1342 CH3 NH Ar3 R11-12 1381 CH3 NH Art R11-16 1343 CH3 NH Ar3 R11-13 1382 CH3 NH Art R11-17 1344 CH3 NH Ar3 R11-14 1383 CH3 NH Art R11-18 1345 CH3 NH Ar3 R11-15 1384 CH3 NH AO R11-19 1346 CH3 NH Ar3 R11-16 1385 CH3 NH Art R11-20 1347 CH3 NH Ar3 R11-17 1386 CH3 NH Art R11-21 1348 CH3 NH Ar3 R11-18 1387 CH3 NH AO R11-22 1349 CH3 NH Ar3 R11-19 1388 CH3 NH AO R11-23 1350 CH3 NH Ar3 R11-20 1389 CH3 NH AO R11-24 1351 CH3 NH Ar3 R11-21 1390 CH3 NH Art R11-25 1352 CH3 NH Ar3 R11-22 1391 CH3 NH AO R11-26 1353 CH3 NH Ar3 R11-23 1392 CH3 NH AO R11-27 1354 CH3 NH Ar3 R11-24 1393 CH3 NH Art R11-28 1355 CH3 NH Ar3 R11-25 1394 CH3 NH Art R11-29 1356 CH3 NH Ar3 R11-26 1395 CH3 NH Art A11-la 1357 CH3 NH Ar3 R11-27 1396 CH3 NH Art A11-lb Line R Q Ar D Line R Q Ar D
1397 CH3 NH AO A11-2a 1436 CH3 NH Ar6 R11-1 1398 CH3 NH AO A11-2b 1437 CH3 NH Ar6 R11-2 1399 CH3 NH Art A11-3a 1438 CH3 NH Ar6 R11-3 1400 CH3 NH Art A11-3b 1439 CH3 NH Ar6 R11-4 1401 CH3 NH Ar5 R11-1 1440 CH3 NH Ar6 R11-5 1402 CH3 NH Ar5 R11-2 1441 CH3 NH Ar6 R11-6 1403 CH3 NH Ar5 R11-3 1442 CH3 NH Ar6 R11-7 1404 CH3 NH Ar5 R11-4 1443 CH3 NH Ar6 R11-8 1405 CH3 NH Ar5 R11-5 1444 CH3 NH Ar6 R11-9 1406 CH3 NH Ar5 R11-6 1445 CH3 NH Ar6 R11-10 1407 CH3 NH Ar5 R11-7 1446 CH3 NH Ar6 R11-11 1408 CH3 NH Ar5 R11-8 1447 CH3 NH Ar6 R11-12 1409 CH3 NH Ar5 R11-9 1448 CH3 NH Ar6 R11-13 1410 CH3 NH Ar5 R11-10 1449 CH3 NH Ar6 R11-14 1411 CH3 NH Ar5 R11-11 1450 CH3 NH Ar6 R11-15 1412 CH3 NH Ar5 R11-12 1451 CH3 NH Ar6 R11-16 1413 CH3 NH Ar5 R11-13 1452 CH3 NH Ar6 R11-17 1414 CH3 NH Ar5 R11-14 1453 CH3 NH Ar6 R11-18 1415 CH3 NH Ar5 R11-15 1454 CH3 NH Ar6 R11-19 1416 CH3 NH Ar5 R11-16 1455 CH3 NH Ar6 R11-20 1417 CH3 NH Ar5 R11-17 1456 CH3 NH Ar6 R11-21 1418 CH3 NH Ar5 R11-18 1457 CH3 NH Ar6 R11-22 1419 CH3 NH Ar5 R11-19 1458 CH3 NH Ar6 R11-23 1420 CH3 NH Ar5 R11-20 1459 CH3 NH Ar6 R11-24 1421 CH3 NH Ar5 R11-21 1460 CH3 NH Ar6 R11-25 1422 CH3 NH Ar5 R11-22 1461 CH3 NH Ar6 R11-26 1423 CH3 NH Ar5 R11-23 1462 CH3 NH Ar6 R11-27 1424 CH3 NH Ar5 R11-24 1463 CH3 NH Ar6 R11-28 1425 CH3 NH Ar5 R11-25 1464 CH3 NH Ar6 R11-29 1426 CH3 NH Ar5 R11-26 1465 CH3 NH Ar6 A11-la 1427 CH3 NH Ar5 R11-27 1466 CH3 NH Ar6 A11-lb 1428 CH3 NH Ar5 R11-28 1467 CH3 NH Ar6 A11-2a 1429 CH3 NH Ar5 R11-29 1468 CH3 NH Ar6 A11-2b 1430 CH3 NH Ar5 A11-la 1469 CH3 NH Ar6 A11-3a 1431 CH3 NH Ar5 A11-lb 1470 CH3 NH Ar6 A11-3b 1432 CH3 NH Ar5 A11-2a 1471 CH3 NH Ar7 R11-1 1433 CH3 NH Ar5 A11-2b 1472 CH3 NH Ar7 R11-2 1434 CH3 NH Ar5 A11-3a 1473 CH3 NH Ar7 R11-3 1435 CH3 NH Ar5 A11-3b 1474 CH3 NH Ar7 R11-4 Line R Q Ar D Line R Q Ar D
1475 CH3 NH AC R11-5 1514 CH3 NH Ar8 R11-9 1476 CH3 NH AC R11-6 1515 CH3 NH Ar8 R11-10 1477 CH3 NH Ar7 R11-7 1516 CH3 NH Ar8 R11-11 1478 CH3 NH Ar7 R11-8 1517 CH3 NH Ar8 R11-12 1479 CH3 NH AC R11-9 1518 CH3 NH Ar8 R11-13 1480 CH3 NH Ar7 R11-10 1519 CH3 NH Ar8 R11-14 1481 CH3 NH Ar7 R11-11 1520 CH3 NH Ar8 R11-15 1482 CH3 NH Ar7 R11-12 1521 CH3 NH Ar8 R11-16 1483 CH3 NH Ar7 R11-13 1522 CH3 NH Ar8 R11-17 1484 CH3 NH Ar7 R11-14 1523 CH3 NH Ar8 R11-18 1485 CH3 NH Ar7 R11-15 1524 CH3 NH Ar8 R11-19 1486 CH3 NH Ar7 R11-16 1525 CH3 NH Ar8 R11-20 1487 CH3 NH Ar7 R11-17 1526 CH3 NH Ar8 R11-21 1488 CH3 NH Ar7 R11-18 1527 CH3 NH Ar8 R11-22 1489 CH3 NH Ar7 R11-19 1528 CH3 NH Ar8 R11-23 1490 CH3 NH Ar7 R11-20 1529 CH3 NH Ar8 R11-24 1491 CH3 NH Ar7 R11-21 1530 CH3 NH Ar8 R11-25 1492 CH3 NH Ar7 R11-22 1531 CH3 NH Ar8 R11-26 1493 CH3 NH Ar7 R11-23 1532 CH3 NH Ar8 R11-27 1494 CH3 NH Ar7 R11-24 1533 CH3 NH Ar8 R11-28 1495 CH3 NH Ar7 R11-25 1534 CH3 NH Ar8 R11-29 1496 CH3 NH Ar7 R11-26 1535 CH3 NH Ar8 A11-la 1497 CH3 NH Ar7 R11-27 1536 CH3 NH Ar8 A11-lb 1498 CH3 NH Ar7 R11-28 1537 CH3 NH Ar8 A11-2a 1499 CH3 NH Ar7 R11-29 1538 CH3 NH Ar8 A11-2b 1500 CH3 NH Ar7 A11-la 1539 CH3 NH Ar8 A11-3a 1501 CH3 NH AC A11-lb 1540 CH3 NH Ar8 A11-3b 1502 CH3 NH Ar7 A11-2a 1541 CH3 NH Ar9 R11-1 1503 CH3 NH Ar7 A11-2b 1542 CH3 NH Ar9 R11-2 1504 CH3 NH AC A11-3a 1543 CH3 NH Ar9 R11-3 1505 CH3 NH AC A11-3b 1544 CH3 NH Ar9 R11-4 1506 CH3 NH Ar8 R11-1 1545 CH3 NH Ar9 R11-5 1507 CH3 NH Ar8 R11-2 1546 CH3 NH Ar9 R11-6 1508 CH3 NH Ar8 R11-3 1547 CH3 NH Ar9 R11-7 1509 CH3 NH Ar8 R11-4 1548 CH3 NH Ar9 R11-8 1510 CH3 NH Ar8 R11-5 1549 CH3 NH Ar9 R11-9 1511 CH3 NH Ar8 R11-6 1550 CH3 NH Ar9 R11-10 1512 CH3 NH Ar8 R11-7 1551 CH3 NH Ar9 R11-11 1513 CH3 NH Ar8 R11-8 1552 CH3 NH Ar9 R11-12 Line R Q Ar D Line R Q Ar D
1553 CH3 NH Ar9 R11-13 1592 CH3 NH Arl R11-17 1554 CH3 NH Ar9 R11-14 1593 CH3 NH Arl R11-18 1555 CH3 NH Ar9 R11-15 1594 CH3 NH Arlo R11-19 1556 CH3 NH Ar9 R11-16 1595 CH3 NH Arlo R11-20 1557 CH3 NH Ar9 R11-17 1596 CH3 NH Arl R11-21 1558 CH3 NH Ar9 R11-18 1597 CH3 NH Arlo R11-22 1559 CH3 NH Ar9 R11-19 1598 CH3 NH Arlo R11-23 1560 CH3 NH Ar9 R11-20 1599 CH3 NH Arlo R11-24 1561 CH3 NH Ar9 R11-21 1600 CH3 NH Arlo R11-25 1562 CH3 NH Ar9 R11-22 1601 CH3 NH Arlo R11-26 1563 CH3 NH Ar9 R11-23 1602 CH3 NH Arlo R11-27 1564 CH3 NH Ar9 R11-24 1603 CH3 NH Arlo R11-28 1565 CH3 NH Ar9 R11-25 1604 CH3 NH Arlo R11-29 1566 CH3 NH Ar9 R11-26 1605 CH3 NH Arlo A11-la 1567 CH3 NH Ar9 R11-27 1606 CH3 NH Arlo A11-lb 1568 CH3 NH Ar9 R11-28 1607 CH3 NH Arlo A11-2a 1569 CH3 NH Ar9 R11-29 1608 CH3 NH Arlo A11-2b 1570 CH3 NH Ar9 A11-la 1609 CH3 NH Arlo A11-3a 1571 CH3 NH Ar9 A11-lb 1610 CH3 NH Arlo A11-3b 1572 CH3 NH Ar9 A11-2a 1611 CH3 NH Aril R11-1 1573 CH3 NH Ar9 A11-2b 1612 CH3 NH Aril R11-2 1574 CH3 NH Ar9 A11-3a 1613 CH3 NH Aril R11-3 1575 CH3 NH Ar9 A11-3b 1614 CH3 NH Aril R11-4 1576 CH3 NH Arlo R11-1 1615 CH3 NH Aril R11-5 1577 CH3 NH Arlo R11-2 1616 CH3 NH Aril R11-6 1578 CH3 NH Arlo R11-3 1617 CH3 NH Aril R11-7 1579 CH3 NH Arl R11-4 1618 CH3 NH Aril R11-8 1580 CH3 NH Arlo R11-5 1619 CH3 NH Aril R11-9 1581 CH3 NH Arlo R11-6 1620 CH3 NH Aril R11-10 1582 CH3 NH Arl R11-7 1621 CH3 NH Aril R11-11 1583 CH3 NH Arl R11-8 1622 CH3 NH Aril R11-12 1584 CH3 NH Arl R11-9 1623 CH3 NH Aril R11-13 1585 CH3 NH Arlo R11-10 1624 CH3 NH Aril R11-14 1586 CH3 NH Arl R11-11 1625 CH3 NH Aril R11-15 1587 CH3 NH Arl R11-12 1626 CH3 NH Aril R11-16 1588 CH3 NH Arlo R11-13 1627 CH3 NH Aril R11-17 1589 CH3 NH Arlo R11-14 1628 CH3 NH Aril R11-18 1590 CH3 NH Arlo R11-15 1629 CH3 NH Aril R11-19 1591 CH3 NH Arlo R11-16 1630 CH3 NH Aril R11-20 Line R Q Ar D Line R Q Ar D
1631 CH3 NH Aril R11-21 1670 CH3 NH Ar12 R11-25 1632 CH3 NH Aril R11-22 1671 CH3 NH Ar12 R11-26 1633 CH3 NH Aril R11-23 1672 CH3 NH Ar12 R11-27 1634 CH3 NH Aril R11-24 1673 CH3 NH Ar12 R11-28 1635 CH3 NH Aril R11-25 1674 CH3 NH Ar12 R11-29 1636 CH3 NH Aril R11-26 1675 CH3 NH Ar12 A11-la 1637 CH3 NH Aril R11-27 1676 CH3 NH Ar12 A11-lb 1638 CH3 NH Aril R11-28 1677 CH3 NH Ar12 A11-2a 1639 CH3 NH Aril R11-29 1678 CH3 NH Ar12 A11-2b 1640 CH3 NH Aril A11-la 1679 CH3 NH Ar12 A11-3a 1641 CH3 NH Aril A11-lb 1680 CH3 NH Ar12 A11-3b 1642 CH3 NH Aril A11-2a 1681 CH3 NCH3 Arl R11-1 1643 CH3 NH Aril A11-2b 1682 CH3 NCH3 Arl R11-2 1644 CH3 NH Aril A11-3a 1683 CH3 NCH3 Arl R11-3 1645 CH3 NH Aril A11-3b 1684 CH3 NCH3 Arl R11-4 1646 CH3 NH Ar12 R11-1 1685 CH3 NCH3 Arl R11-5 1647 CH3 NH Ar12 R11-2 1686 CH3 NCH3 Arl R11-6 1648 CH3 NH Ar12 R11-3 1687 CH3 NCH3 Arl R11-7 1649 CH3 NH Ar12 R11-4 1688 CH3 NCH3 Arl R11-8 1650 CH3 NH Ar12 R11-5 1689 CH3 NCH3 Arl R11-9 1651 CH3 NH Ar12 R11-6 1690 CH3 NCH3 Arl R11-10 1652 CH3 NH Ar12 R11-7 1691 CH3 NCH3 Arl R11-11 1653 CH3 NH Ar12 R11-8 1692 CH3 NCH3 Arl R11-12 1654 CH3 NH Ar12 R11-9 1693 CH3 NCH3 Arl R11-13 1655 CH3 NH Ar12 R11-10 1694 CH3 NCH3 Arl R11-14 1656 CH3 NH Ar12 R11-11 1695 CH3 NCH3 Arl R11-15 1657 CH3 NH Ar12 R11-12 1696 CH3 NCH3 Arl R11-16 1658 CH3 NH Ar12 R11-13 1697 CH3 NCH3 Arl R11-17 1659 CH3 NH Ar12 R11-14 1698 CH3 NCH3 Arl R11-18 1660 CH3 NH Ar12 R11-15 1699 CH3 NCH3 Arl R11-19 1661 CH3 NH Ar12 R11-16 1700 CH3 NCH3 Arl R11-20 1662 CH3 NH Ar12 R11-17 1701 CH3 NCH3 Arl R11-21 1663 CH3 NH Ar12 R11-18 1702 CH3 NCH3 Arl R11-22 1664 CH3 NH Ar12 R11-19 1703 CH3 NCH3 Arl R11-23 1665 CH3 NH Ar12 R11-20 1704 CH3 NCH3 Arl R11-24 1666 CH3 NH Ar12 R11-21 1705 CH3 NCH3 Arl R11-25 1667 CH3 NH Ar12 R11-22 1706 CH3 NCH3 Arl R11-26 1668 CH3 NH Ar12 R11-23 1707 CH3 NCH3 Arl R11-27 1669 CH3 NH Ar12 R11-24 1708 CH3 NCH3 Arl R11-28 Line R Q Ar D Line R Q Ar D
1709 CH3 NCH3 Arl R11-29 1748 CH3 NCH3 Ar2 A11-2b 1710 CH3 NCH3 Arl A11-la 1749 CH3 NCH3 Ar2 A11-3a 1711 CH3 NCH3 Arl A11-lb 1750 CH3 NCH3 Ar2 A11-3b 1712 CH3 NCH3 Arl A11-2a 1751 CH3 NCH3 Ar3 R11-1 1713 CH3 NCH3 Arl A11-2b 1752 CH3 NCH3 Ar3 R11-2 1714 CH3 NCH3 Arl A11-3a 1753 CH3 NCH3 Ar3 R11-3 1715 CH3 NCH3 Arl A11-3b 1754 CH3 NCH3 Ar3 R11-4 1716 CH3 NCH3 Ar2 R11-1 1755 CH3 NCH3 Ar3 R11-5 1717 CH3 NCH3 Ar2 R11-2 1756 CH3 NCH3 Ar3 R11-6 1718 CH3 NCH3 Ar2 R11-3 1757 CH3 NCH3 Ar3 R11-7 1719 CH3 NCH3 Ar2 R11-4 1758 CH3 NCH3 Ar3 R11-8 1720 CH3 NCH3 Ar2 R11-5 1759 CH3 NCH3 Ar3 R11-9 1721 CH3 NCH3 Ar2 R11-6 1760 CH3 NCH3 Ar3 R11-10 1722 CH3 NCH3 Ar2 R11-7 1761 CH3 NCH3 Ar3 R11-11 1723 CH3 NCH3 Ar2 R11-8 1762 CH3 NCH3 Ar3 R11-12 1724 CH3 NCH3 Ar2 R11-9 1763 CH3 NCH3 Ar3 R11-13 1725 CH3 NCH3 Ar2 R11-10 1764 CH3 NCH3 Ar3 R11-14 1726 CH3 NCH3 Ar2 R11-11 1765 CH3 NCH3 Ar3 R11-15 1727 CH3 NCH3 Ar2 R11-12 1766 CH3 NCH3 Ar3 R11-16 1728 CH3 NCH3 Ar2 R11-13 1767 CH3 NCH3 Ar3 R11-17 1729 CH3 NCH3 Ar2 R11-14 1768 CH3 NCH3 Ar3 R11-18 1730 CH3 NCH3 Ar2 R11-15 1769 CH3 NCH3 Ar3 R11-19 1731 CH3 NCH3 Ar2 R11-16 1770 CH3 NCH3 Ar3 R11-20 1732 CH3 NCH3 Ar2 R11-17 1771 CH3 NCH3 Ar3 R11-21 1733 CH3 NCH3 Ar2 R11-18 1772 CH3 NCH3 Ar3 R11-22 1734 CH3 NCH3 Ar2 R11-19 1773 CH3 NCH3 Ar3 R11-23 1735 CH3 NCH3 Ar2 R11-20 1774 CH3 NCH3 Ar3 R11-24 1736 CH3 NCH3 Ar2 R11-21 1775 CH3 NCH3 Ar3 R11-25 1737 CH3 NCH3 Ar2 R11-22 1776 CH3 NCH3 Ar3 R11-26 1738 CH3 NCH3 Ar2 R11-23 1777 CH3 NCH3 Ar3 R11-27 1739 CH3 NCH3 Ar2 R11-24 1778 CH3 NCH3 Ar3 R11-28 1740 CH3 NCH3 Ar2 R11-25 1779 CH3 NCH3 Ar3 R11-29 1741 CH3 NCH3 Ar2 R11-26 1780 CH3 NCH3 Ar3 A11-la 1742 CH3 NCH3 Ar2 R11-27 1781 CH3 NCH3 Ar3 A11-lb 1743 CH3 NCH3 Ar2 R11-28 1782 CH3 NCH3 Ar3 A11-2a 1744 CH3 NCH3 Ar2 R11-29 1783 CH3 NCH3 Ar3 A11-2b 1745 CH3 NCH3 Ar2 A11-la 1784 CH3 NCH3 Ar3 A11-3a 1746 CH3 NCH3 Ar2 A11-lb 1785 CH3 NCH3 Ar4 A11-3b 1747 CH3 NCH3 Ar2 A11-2a 1786 CH3 NCH3 Ar4 R11-1 Line R Q Ar D Line R Q Ar D
1787 CH3 NCH3 AO R11-2 1826 CH3 NCH3 Ar5 R11-6 1788 CH3 NCH3 AO R11-3 1827 CH3 NCH3 Ar5 R11-7 1789 CH3 NCH3 Art R11-4 1828 CH3 NCH3 Ar5 R11-8 1790 CH3 NCH3 Art R11-5 1829 CH3 NCH3 Ar5 R11-9 1791 CH3 NCH3 AO R11-6 1830 CH3 NCH3 Ar5 R11-10 1792 CH3 NCH3 Art R11-7 1831 CH3 NCH3 Ar5 R11-11 1793 CH3 NCH3 Art R11-8 1832 CH3 NCH3 Ar5 R11-12 1794 CH3 NCH3 Art R11-9 1833 CH3 NCH3 Ar5 R11-13 1795 CH3 NCH3 Art R11-10 1834 CH3 NCH3 Ar5 R11-14 1796 CH3 NCH3 Art R11-11 1835 CH3 NCH3 Ar5 R11-15 1797 CH3 NCH3 Art R11-12 1836 CH3 NCH3 Ar5 R11-16 1798 CH3 NCH3 Art R11-13 1837 CH3 NCH3 Ar5 R11-17 1799 CH3 NCH3 Art R11-14 1838 CH3 NCH3 Ar5 R11-18 1800 CH3 NCH3 Art R11-15 1839 CH3 NCH3 Ar5 R11-19 1801 CH3 NCH3 Art R11-16 1840 CH3 NCH3 Ar5 R11-20 1802 CH3 NCH3 Art R11-17 1841 CH3 NCH3 Ar5 R11-21 1803 CH3 NCH3 Art R11-18 1842 CH3 NCH3 Ar5 R11-22 1804 CH3 NCH3 Art R11-19 1843 CH3 NCH3 Ar5 R11-23 1805 CH3 NCH3 Art R11-20 1844 CH3 NCH3 Ar5 R11-24 1806 CH3 NCH3 Art R11-21 1845 CH3 NCH3 Ar5 R11-25 1807 CH3 NCH3 Art R11-22 1846 CH3 NCH3 Ar5 R11-26 1808 CH3 NCH3 Art R11-23 1847 CH3 NCH3 Ar5 R11-27 1809 CH3 NCH3 Art R11-24 1848 CH3 NCH3 Ar5 R11-28 1810 CH3 NCH3 Art R11-25 1849 CH3 NCH3 Ar5 R11-29 1811 CH3 NCH3 Art R11-26 1850 CH3 NCH3 Ar5 A11-la 1812 CH3 NCH3 Art R11-27 1851 CH3 NCH3 Ar5 A11-lb 1813 CH3 NCH3 AO R11-28 1852 CH3 NCH3 Ar5 A11-2a 1814 CH3 NCH3 Art R11-29 1853 CH3 NCH3 Ar5 A11-2b 1815 CH3 NCH3 Art A11-la 1854 CH3 NCH3 Ar5 A11-3a 1816 CH3 NCH3 AO A11-lb 1855 CH3 NCH3 Ar5 A11-3b 1817 CH3 NCH3 AO A11-2a 1856 CH3 NCH3 Ar6 R11-1 1818 CH3 NCH3 AO A11-2b 1857 CH3 NCH3 Ar6 R11-2 1819 CH3 NCH3 Art A11-3a 1858 CH3 NCH3 Ar6 R11-3 1820 CH3 NCH3 AO A11-3b 1859 CH3 NCH3 Ar6 R11-4 1821 CH3 NCH3 Ar5 R11-1 1860 CH3 NCH3 Ar6 R11-5 1822 CH3 NCH3 Ar5 R11-2 1861 CH3 NCH3 Ar6 R11-6 1823 CH3 NCH3 Ar5 R11-3 1862 CH3 NCH3 Ar6 R11-7 1824 CH3 NCH3 Ar5 R11-4 1863 CH3 NCH3 Ar6 R11-8 1825 CH3 NCH3 Ar5 R11-5 1864 CH3 NCH3 Ar6 R11-9 Line R Q Ar D Line R Q Ar D
1865 CH3 NCH3 Ar6 R11-10 1904 CH3 NCH3 Ar7 R11-14 1866 CH3 NCH3 Ar6 R11-11 1905 CH3 NCH3 Ar7 R11-15 1867 CH3 NCH3 Ar6 R11-12 1906 CH3 NCH3 Ar7 R11-16 1868 CH3 NCH3 Ar6 R11-13 1907 CH3 NCH3 Ar7 R11-17 1869 CH3 NCH3 Ar6 R11-14 1908 CH3 NCH3 Ar7 R11-18 1870 CH3 NCH3 Ar6 R11-15 1909 CH3 NCH3 Ar7 R11- 1 9 1871 CH3 NCH3 Ar6 R11-16 1910 CH3 NCH3 Ar7 R11-20 1872 CH3 NCH3 Ar6 R11-17 1911 CH3 NCH3 Ar7 R11-21 1873 CH3 NCH3 Ar6 R11-18 1912 CH3 NCH3 Ar7 R11-22 1874 CH3 NCH3 Ar6 R11-19 1913 CH3 NCH3 Ar7 R11-23 1875 CH3 NCH3 Ar6 R11-20 1914 CH3 NCH3 Ar7 R11-24 1876 CH3 NCH3 Ar6 R11-21 1915 CH3 NCH3 Ar7 R11-25 1877 CH3 NCH3 Ar6 R11-22 1916 CH3 NCH3 Ar7 R11-26 1878 CH3 NCH3 Ar6 R11-23 1917 CH3 NCH3 Ar7 R11-27 1879 CH3 NCH3 Ar6 R11-24 1918 CH3 NCH3 Ar7 R11-28 1880 CH3 NCH3 Ar6 R11-25 1919 CH3 NCH3 Ar7 R11-29 1881 CH3 NCH3 Ar6 R11-26 1920 CH3 NCH3 Ar7 A11-la 1882 CH3 NCH3 Ar6 R11-27 1921 CH3 NCH3 Ar7 A11-lb 1883 CH3 NCH3 Ar6 R11-28 1922 CH3 NCH3 Ar7 A11-2a 1884 CH3 NCH3 Ar6 R11-29 1923 CH3 NCH3 Ar7 A11-2b 1885 CH3 NCH3 Ar6 A11-la 1924 CH3 NCH3 Ar7 A11-3a 1886 CH3 NCH3 Ar6 A11-lb 1925 CH3 NCH3 Ar7 A11-3b 1887 CH3 NCH3 Ar6 A11-2a 1926 CH3 NCH3 Ar8 R11-1 1888 CH3 NCH3 Ar6 A11-2b 1927 CH3 NCH3 Ar8 R11-2 1889 CH3 NCH3 Ar6 A11-3a 1928 CH3 NCH3 Ar8 R11-3 1890 CH3 NCH3 Ar6 A11-3b 1929 CH3 NCH3 Ar8 R11-4 1891 CH3 NCH3 Ar7 R11-1 1930 CH3 NCH3 AO R11-5 1892 CH3 NCH3 Ar7 R11-2 1931 CH3 NCH3 Ar8 R11-6 1893 CH3 NCH3 Ar7 R11-3 1932 CH3 NCH3 Ar8 R11-7 1894 CH3 NCH3 Ar7 R11-4 1933 CH3 NCH3 AO R11-8 1895 CH3 NCH3 Ar7 R11-5 1934 CH3 NCH3 AO R11-9 1896 CH3 NCH3 Ar7 R11-6 1935 CH3 NCH3 AO R11- 1 0 1897 CH3 NCH3 Ar7 R11-7 1936 CH3 NCH3 Ar8 R11-11 1898 CH3 NCH3 Ar7 R11-8 1937 CH3 NCH3 AO R11-12 1899 CH3 NCH3 Ar7 R11-9 1938 CH3 NCH3 AO R11- 1 3 1900 CH3 NCH3 Ar7 R11-10 1939 CH3 NCH3 Ar8 R11-14 1901 CH3 NCH3 Ar7 R11-11 1940 CH3 NCH3 Ar8 R11- 1 5 1902 CH3 NCH3 Ar7 R11- 1 2 1941 CH3 NCH3 Ar8 R11- 1 6 1903 CH3 NCH3 Ar7 R11-13 1942 CH3 NCH3 Ar8 R11- 1 7 Line R Q Ar D Line R Q Ar D
1943 CH3 NCH3 Ar8 R11-18 1982 CH3 NCH3 Ar9 R11-22 1944 CH3 NCH3 Ar8 R11-19 1983 CH3 NCH3 Ar9 R11-23 1945 CH3 NCH3 Ar8 R11-20 1984 CH3 NCH3 Ar9 R11-24 1946 CH3 NCH3 Ar8 R11-21 1985 CH3 NCH3 Ar9 R11-25 1947 CH3 NCH3 Ar8 R11-22 1986 CH3 NCH3 Ar9 R11-26 1948 CH3 NCH3 Ar8 R11-23 1987 CH3 NCH3 Ar9 R11-27 1949 CH3 NCH3 Ar8 R11-24 1988 CH3 NCH3 Ar9 R11-28 1950 CH3 NCH3 Ar8 R11-25 1989 CH3 NCH3 Ar9 R11-29 1951 CH3 NCH3 Ar8 R11-26 1990 CH3 NCH3 Ar9 A11-la 1952 CH3 NCH3 Ar8 R11-27 1991 CH3 NCH3 Ar9 A11-lb 1953 CH3 NCH3 Ar8 R11-28 1992 CH3 NCH3 Ar9 A11-2a 1954 CH3 NCH3 Ar8 R11-29 1993 CH3 NCH3 Ar9 A11-2b 1955 CH3 NCH3 Ar8 A11-la 1994 CH3 NCH3 Ar9 A11-3a 1956 CH3 NCH3 Ar8 A11-lb 1995 CH3 NCH3 Ar9 A11-3b 1957 CH3 NCH3 Ar8 A11-2a 1996 CH3 NCH3 Arlo R11-1 1958 CH3 NCH3 Ar8 A11-2b 1997 CH3 NCH3 Arlo R11-2 1959 CH3 NCH3 Ar8 A11-3a 1998 CH3 NCH3 Arlo R11-3 1960 CH3 NCH3 Ar8 A11-3b 1999 CH3 NCH3 Arlo R11-4 1961 CH3 NCH3 Ar9 R11-1 2000 CH3 NCH3 Arlo R11-5 1962 CH3 NCH3 Ar9 R11-2 2001 CH3 NCH3 Arlo R11-6 1963 CH3 NCH3 Ar9 R11-3 2002 CH3 NCH3 Arlo R11-7 1964 CH3 NCH3 Ar9 R11-4 2003 CH3 NCH3 Arlo R11-8 1965 CH3 NCH3 Ar9 R11-5 2004 CH3 NCH3 Arlo R11-9 1966 CH3 NCH3 Ar9 R11-6 2005 CH3 NCH3 Arlo R11-10 1967 CH3 NCH3 Ar9 R11-7 2006 CH3 NCH3 Arlo R11-11 1968 CH3 NCH3 Ar9 R11-8 2007 CH3 NCH3 Arlo R11-12 1969 CH3 NCH3 Ar9 R11-9 2008 CH3 NCH3 Arl R11-13 1970 CH3 NCH3 Ar9 R11-10 2009 CH3 NCH3 Arlo R11-14 1971 CH3 NCH3 Ar9 R11-11 2010 CH3 NCH3 Arlo R11-15 1972 CH3 NCH3 Ar9 R11-12 2011 CH3 NCH3 Arl R11-16 1973 CH3 NCH3 Ar9 R11-13 2012 CH3 NCH3 Arl R11-17 1974 CH3 NCH3 Ar9 R11-14 2013 CH3 NCH3 Arl R11-18 1975 CH3 NCH3 Ar9 R11-15 2014 CH3 NCH3 Arlo R11-19 1976 CH3 NCH3 Ar9 R11-16 2015 CH3 NCH3 Arl R11-20 1977 CH3 NCH3 Ar9 R11-17 2016 CH3 NCH3 Arl R11-21 1978 CH3 NCH3 Ar9 R11-18 2017 CH3 NCH3 Arlo R11-22 1979 CH3 NCH3 Ar9 R11-19 2018 CH3 NCH3 Arlo R11-23 1980 CH3 NCH3 Ar9 R11-20 2019 CH3 NCH3 Arlo R11-24 1981 CH3 NCH3 Ar9 R11-21 2020 CH3 NCH3 Arlo R11-25 Line R Q Ar D Line R Q Ar D
2021 CH3 NCH3 Arl R11-26 2060 CH3 NCH3 Aril A11-la 2022 CH3 NCH3 Arl R11-27 2061 CH3 NCH3 Aril A11-lb 2023 CH3 NCH3 Arlo R11-28 2062 CH3 NCH3 Aril A11-2a 2024 CH3 NCH3 Arlo R11-29 2063 CH3 NCH3 Aril A11-2b 2025 CH3 NCH3 Arl A11-la 2064 CH3 NCH3 Aril A11-3a 2026 CH3 NCH3 Arlo A11-lb 2065 CH3 NCH3 Aril A11-3b 2027 CH3 NCH3 Arlo A11-2a 2066 CH3 NCH3 Ar12 R11-1 2028 CH3 NCH3 Arlo A11-2b 2067 CH3 NCH3 Ar12 R11-2 2029 CH3 NCH3 Arlo A11-3a 2068 CH3 NCH3 Ar12 R11-3 2030 CH3 NCH3 Arlo A11-3b 2069 CH3 NCH3 Ar12 R11-4 2031 CH3 NCH3 Aril R11-1 2070 CH3 NCH3 Ar12 R11-5 2032 CH3 NCH3 Aril R11-2 2071 CH3 NCH3 Ar12 R11-6 2033 CH3 NCH3 Aril R11-3 2072 CH3 NCH3 Ar12 R11-7 2034 CH3 NCH3 Aril R11-4 2073 CH3 NCH3 Ar12 R11-8 2035 CH3 NCH3 Aril R11-5 2074 CH3 NCH3 Ar12 R11-9 2036 CH3 NCH3 Aril R11-6 2075 CH3 NCH3 Ar12 R11-10 2037 CH3 NCH3 Aril R11-7 2076 CH3 NCH3 Ar12 R11-11 2038 CH3 NCH3 Aril R11-8 2077 CH3 NCH3 Ar12 R11-12 2039 CH3 NCH3 Aril R11-9 2078 CH3 NCH3 Ar12 R11-13 2040 CH3 NCH3 Aril R11-10 2079 CH3 NCH3 Ar12 R11-14 2041 CH3 NCH3 Aril R11-11 2080 CH3 NCH3 Ar12 R11-15 2042 CH3 NCH3 Aril R11-12 2081 CH3 NCH3 Ar12 R11-16 2043 CH3 NCH3 Aril R11-13 2082 CH3 NCH3 Ar12 R11-17 2044 CH3 NCH3 Aril R11-14 2083 CH3 NCH3 Ar12 R11-18 2045 CH3 NCH3 Aril R11-15 2084 CH3 NCH3 Ar12 R11-19 2046 CH3 NCH3 Aril R11-16 2085 CH3 NCH3 Ar12 R11-20 2047 CH3 NCH3 Aril R11-17 2086 CH3 NCH3 Ar12 R11-21 2048 CH3 NCH3 Aril R11-18 2087 CH3 NCH3 Ar12 R11-22 2049 CH3 NCH3 Aril R11-19 2088 CH3 NCH3 Ar12 R11-23 2050 CH3 NCH3 Aril R11-20 2089 CH3 NCH3 Ar12 R11-24 2051 CH3 NCH3 Aril R11-21 2090 CH3 NCH3 Ar12 R11-25 2052 CH3 NCH3 Aril R11-22 2091 CH3 NCH3 Ar12 R11-26 2053 CH3 NCH3 Aril R11-23 2092 CH3 NCH3 Ar12 R11-27 2054 CH3 NCH3 Aril R11-24 2093 CH3 NCH3 Ar12 R11-28 2055 CH3 NCH3 Aril R11-25 2094 CH3 NCH3 Ar12 R11-29 2056 CH3 NCH3 Aril R11-26 2095 CH3 NCH3 Ar12 A11-la 2057 CH3 NCH3 Aril R11-27 2096 CH3 NCH3 Ar12 A11-lb 2058 CH3 NCH3 Aril R11-28 2097 CH3 NCH3 Ar12 A11-2a 2059 CH3 NCH3 Aril R11-29 2098 CH3 NCH3 Ar12 A11-2b Line R Q Ar D Line R Q Ar D
2099 CH3 NCH3 Ar12 A11-3a 2138 CH3 0 Ar2 R11-3 2100 CH3 NCH3 Ar12 A11-3b 2139 CH3 0 Ar2 R11-4 2101 CH3 0 Arl R11-1 2140 CH3 0 Ar2 R11-5 2102 CH3 0 Arl R11-2 2141 CH3 0 Ar2 R11-6 2103 CH3 0 Arl R11-3 2142 CH3 0 Ar2 R11-7 2104 CH3 0 Arl R11-4 2143 CH3 0 Ar2 R11-8 2105 CH3 0 Arl R11-5 2144 CH3 0 Ar2 R11-9 2106 CH3 0 Arl R11-6 2145 CH3 0 Ar2 R11-10 2107 CH3 0 Arl R11-7 2146 CH3 0 Ar2 R11-11 2108 CH3 0 Arl R11-8 2147 CH3 0 Ar2 R11-12 2109 CH3 0 Arl R11-9 2148 CH3 0 Ar2 R11-13 2110 CH3 0 Arl R11-10 2149 CH3 0 Ar2 R11-14 2111 CH3 0 Arl R11-11 2150 CH3 0 Ar2 R11-15 2112 CH3 0 Arl R11-12 2151 CH3 0 Ar2 R11-16 2113 CH3 0 Arl R11-13 2152 CH3 0 Ar2 R11-17 2114 CH3 0 Arl R11-14 2153 CH3 0 Ar2 R11-18 2115 CH3 0 Arl R11-15 2154 CH3 0 Ar2 R11-19 2116 CH3 0 Arl R11-16 2155 CH3 0 Ar2 R11-20 2117 CH3 0 Arl R11-17 2156 CH3 0 Ar2 R11-21 2118 CH3 0 Arl R11-18 2157 CH3 0 Ar2 R11-22 2119 CH3 0 Arl R11-19 2158 CH3 0 Ar2 R11-23 2120 CH3 0 Arl R11-20 2159 CH3 0 Ar2 R11-24 2121 CH3 0 Arl R11-21 2160 CH3 0 Ar2 R11-25 2122 CH3 0 Arl R11-22 2161 CH3 0 Ar2 R11-26 2123 CH3 0 Arl R11-23 2162 CH3 0 Ar2 R11-27 2124 CH3 0 Arl R11-24 2163 CH3 0 Ar2 R11-28 2125 CH3 0 Arl R11-25 2164 CH3 0 Ar2 R11-29 2126 CH3 0 Arl R11-26 2165 CH3 0 Ar2 A11-la 2127 CH3 0 Arl R11-27 2166 CH3 0 Ar2 A11-lb 2128 CH3 0 Arl R11-28 2167 CH3 0 Ar2 A11-2a 2129 CH3 0 Arl R11-29 2168 CH3 0 Ar2 A11-2b 2130 CH3 0 Arl A11-la 2169 CH3 0 Ar2 A11-3a 2131 CH3 0 Arl A11-lb 2170 CH3 0 Ar2 A11-3b 2132 CH3 0 Arl A11-2a 2171 CH3 0 Ar3 R11-1 2133 CH3 0 Arl A11-2b 2172 CH3 0 Ar3 R11-2 2134 CH3 0 Arl A11-3a 2173 CH3 0 Ar3 R11-3 2135 CH3 0 Arl A11-3b 2174 CH3 0 Ar3 R11-4 2136 CH3 0 Ar2 R11-1 2175 CH3 0 Ar3 R11-5 2137 CH3 0 Ar2 R11-2 2176 CH3 0 Ar3 R11-6 Line R Q Ar D Line R Q Ar D
2177 CH3 0 Ar3 R11-7 2216 CH3 0 Ar4 R11-11 2178 CH3 0 Ar3 R11-8 2217 CH3 0 Ar4 R11-12 2179 CH3 0 Ar3 R11-9 2218 CH3 0 Ar4 R11-13 2180 CH3 0 Ar3 R11-10 2219 CH3 0 Ar4 R11-14 2181 CH3 0 Ar3 R11-11 2220 CH3 0 Ar4 R11-15 2182 CH3 0 Ar3 R11-12 2221 CH3 0 Ar4 R11-16 2183 CH3 0 Ar3 R11-13 2222 CH3 0 Ar4 R11-17 2184 CH3 0 Ar3 R11-14 2223 CH3 0 Ar4 R11-18 2185 CH3 0 Ar3 R11-15 2224 CH3 0 Ar4 R11-19 2186 CH3 0 Ar3 R11-16 2225 CH3 0 Ar4 R11-20 2187 CH3 0 Ar3 R11-17 2226 CH3 0 Ar4 R11-21 2188 CH3 0 Ar3 R11-18 2227 CH3 0 Ar4 R11-22 2189 CH3 0 Ar3 R11-19 2228 CH3 0 Ar4 R11-23 2190 CH3 0 Ar3 R11-20 2229 CH3 0 Ar4 R11-24 2191 CH3 0 Ar3 R11-21 2230 CH3 0 Ar4 R11-25 2192 CH3 0 Ar3 R11-22 2231 CH3 0 Ar4 R11-26 2193 CH3 0 Ar3 R11-23 2232 CH3 0 Ar4 R11-27 2194 CH3 0 Ar3 R11-24 2233 CH3 0 Ar4 R11-28 2195 CH3 0 Ar3 R11-25 2234 CH3 0 Ar4 R11-29 2196 CH3 0 Ar3 R11-26 2235 CH3 0 Ar4 A11-la 2197 CH3 0 Ar3 R11-27 2236 CH3 0 Ar4 A11-lb 2198 CH3 0 Ar3 R11-28 2237 CH3 0 Ar4 A11-2a 2199 CH3 0 Ar3 R11-29 2238 CH3 0 Ar4 A11-2b 2200 CH3 0 Ar3 A11-la 2239 CH3 0 Ar4 A11-3a 2201 CH3 0 Ar3 A11-lb 2240 CH3 0 Ar4 A11-3b 2202 CH3 0 Ar3 A11-2a 2241 CH3 0 Ar5 R11-1 2203 CH3 0 Ar3 A11-2b 2242 CH3 0 Ar5 R11-2 2204 CH3 0 Ar3 A11-3a 2243 CH3 0 Ar5 R11-3 2205 CH3 0 Ar4 A11-3b 2244 CH3 0 Ar5 R11-4 2206 CH3 0 AO R11-1 2245 CH3 0 Ar5 R11-5 2207 CH3 0 AO R11-2 2246 CH3 0 Ar5 R11-6 2208 CH3 0 AO R11-3 2247 CH3 0 Ar5 R11-7 2209 CH3 0 Art R11-4 2248 CH3 0 Ar5 R11-8 2210 CH3 0 AO R11-5 2249 CH3 0 Ar5 R11-9 2211 CH3 0 AO R11-6 2250 CH3 0 Ar5 R11-10 2212 CH3 0 Art R11-7 2251 CH3 0 Ar5 R11-11 2213 CH3 0 Art R11-8 2252 CH3 0 Ar5 R11-12 2214 CH3 0 Art R11-9 2253 CH3 0 Ar5 R11-13 2215 CH3 0 Art R11-10 2254 CH3 0 Ar5 R11-14 Line R Q Ar D Line R Q Ar D
2255 CH3 0 Ar5 R11-15 2294 CH3 0 Ar6 R11-19 2256 CH3 0 Ar5 R11-16 2295 CH3 0 Ar6 R11-20 2257 CH3 0 Ar5 R11-17 2296 CH3 0 Ar6 R11-21 2258 CH3 0 Ar5 R11-18 2297 CH3 0 Ar6 R11-22 2259 CH3 0 Ar5 R11-19 2298 CH3 0 Ar6 R11-23 2260 CH3 0 Ar5 R11-20 2299 CH3 0 Ar6 R11-24 2261 CH3 0 Ar5 R11-21 2300 CH3 0 Ar6 R11-25 2262 CH3 0 Ar5 R11-22 2301 CH3 0 Ar6 R11-26 2263 CH3 0 Ar5 R11-23 2302 CH3 0 Ar6 R11-27 2264 CH3 0 Ar5 R11-24 2303 CH3 0 Ar6 R11-28 2265 CH3 0 Ar5 R11-25 2304 CH3 0 Ar6 R11-29 2266 CH3 0 Ar5 R11-26 2305 CH3 0 Ar6 A11-la 2267 CH3 0 Ar5 R11-27 2306 CH3 0 Ar6 A11-lb 2268 CH3 0 Ar5 R11-28 2307 CH3 0 Ar6 A11-2a 2269 CH3 0 Ar5 R11-29 2308 CH3 0 Ar6 A11-2b 2270 CH3 0 Ar5 A11-la 2309 CH3 0 Ar6 A11-3a 2271 CH3 0 Ar5 A11-lb 2310 CH3 0 Ar6 A11-3b 2272 CH3 0 Ar5 A11-2a 2311 CH3 0 Ar7 R11-1 2273 CH3 0 Ar5 A11-2b 2312 CH3 0 Ar7 R11-2 2274 CH3 0 Ar5 A11-3a 2313 CH3 0 Ar7 R11-3 2275 CH3 0 Ar5 A11-3b 2314 CH3 0 Ar7 R11-4 2276 CH3 0 Ar6 R11-1 2315 CH3 0 Ar7 R11-5 2277 CH3 0 Ar6 R11-2 2316 CH3 0 Ar7 R11-6 2278 CH3 0 Ar6 R11-3 2317 CH3 0 Ar7 R11-7 2279 CH3 0 Ar6 R11-4 2318 CH3 0 Ar7 R11-8 2280 CH3 0 Ar6 R11-5 2319 CH3 0 Ar7 R11-9 2281 CH3 0 Ar6 R11-6 2320 CH3 0 Ar7 R11-10 2282 CH3 0 Ar6 R11-7 2321 CH3 0 Ar7 R11-11 2283 CH3 0 Ar6 R11-8 2322 CH3 0 Ar7 R11-12 2284 CH3 0 Ar6 R11-9 2323 CH3 0 Ar7 R11-13 2285 CH3 0 Ar6 R11-10 2324 CH3 0 Ar7 R11-14 2286 CH3 0 Ar6 R11-11 2325 CH3 0 Ar7 R11-15 2287 CH3 0 Ar6 R11-12 2326 CH3 0 Ar7 R11-16 2288 CH3 0 Ar6 R11-13 2327 CH3 0 Ar7 R11-17 2289 CH3 0 Ar6 R11-14 2328 CH3 0 Ar7 R11-18 2290 CH3 0 Ar6 R11-15 2329 CH3 0 Ar7 R11-19 2291 CH3 0 Ar6 R11-16 2330 CH3 0 Ar7 R11-20 2292 CH3 0 Ar6 R11-17 2331 CH3 0 Ar7 R11-21 2293 CH3 0 Ar6 R11-18 2332 CH3 0 Ar7 R11-22 Line R Q Ar D Line R Q Ar D
2335 CH3 0 Ar7 R11-25 2374 CH3 0 Ar8 R11-29 2336 CH3 0 Ar7 R11-26 2375 CH3 0 Ar8 A11-la 2337 CH3 0 AC R11-27 2376 CH3 0 AO A11-lb 2338 CH3 0 Ar7 R11-28 2377 CH3 0 Ar8 A11-2a 2339 CH3 0 Ar7 R11-29 2378 CH3 0 Ar8 A11-21D
2340 CH3 0 Ar7 A11-la 2379 CH3 0 Ar8 A11-3a 2341 CH3 0 Ar7 A11-lb 2380 CH3 0 Ar8 A11-31D
2342 CH3 0 Ar7 A11-2a 2381 CH3 0 Ar8 R11-1 2343 CH3 0 Ar7 A11-2b 2382 CH3 0 Ar8 R11-2 2344 CH3 0 Ar7 A11-3a 2383 CH3 0 Ar8 R11-3 2345 CH3 0 Ar7 A11-3b 2384 CH3 0 Ar9 R11-4 2346 CH3 0 Ar8 R11-1 2385 CH3 0 Ar9 R11-5 2347 CH3 0 Ar8 R11-2 2386 CH3 0 Ar9 R11-6 2348 CH3 0 Ar8 R11-3 2387 CH3 0 Ar9 R11-7 2349 CH3 0 Ar8 R11-4 2388 CH3 0 Ar9 R11-8 2350 CH3 0 Ar8 R11-5 2389 CH3 0 Ar9 R11-9 2351 CH3 0 Ar8 R11-6 2390 CH3 0 Ar9 R11-10 2352 CH3 0 Ar8 R11-7 2391 CH3 0 Ar9 R11-11 2353 CH3 0 Ar8 R11-8 2392 CH3 0 Ar9 R11-12 2354 CH3 0 Ar8 R11-9 2393 CH3 0 Ar9 R11-13 2355 CH3 0 Ar8 R11-10 2394 CH3 0 Ar9 R11-14 2356 CH3 0 Ar8 R11-11 2395 CH3 0 Ar9 R11-15 2357 CH3 0 Ar8 R11-12 2396 CH3 0 Ar9 R11-16 2358 CH3 0 Ar8 R11-13 2397 CH3 0 Ar9 R11-17 2359 CH3 0 Ar8 R11-14 2398 CH3 0 Ar9 R11-18 2360 CH3 0 Ar8 R11-15 2399 CH3 0 Ar9 R11-19 2361 CH3 0 Ar8 R11-16 2400 CH3 0 Ar9 R11-20 2362 CH3 0 Ar8 R11-17 2401 CH3 0 Ar9 R11-21 2363 CH3 0 Ar8 R11-18 2402 CH3 0 Ar9 R11-22 2364 CH3 0 Ar8 R11-19 2403 CH3 0 Ar9 R11-23 2365 CH3 0 Ar8 R11-20 2404 CH3 0 Ar9 R11-24 2366 CH3 0 Ar8 R11-21 2405 CH3 0 Ar9 R11-25 2367 CH3 0 Ar8 R11-22 2406 CH3 0 Ar9 R11-26 2368 CH3 0 Ar8 R11-23 2407 CH3 0 Ar9 R11-27 2369 CH3 0 Ar8 R11-24 2408 CH3 0 Ar9 R11-28 2370 CH3 0 Ar8 R11-25 2409 CH3 0 Ar9 R11-29 2371 CH3 0 Ar8 R11-26 2410 CH3 0 Ar9 A11-la Line R Q Ar D Line R Q Ar D
2411 CH3 0 Ar9 A11-lb 2450 CH3 0 Arl A11-3b 2412 CH3 0 Ar9 A11-2a 2451 CH3 0 Aril R11-1 2413 CH3 0 Ar9 A11-2b 2452 CH3 0 Aril R11-2 2414 CH3 0 Ar9 A11-3a 2453 CH3 0 Aril R11-3 2415 CH3 0 Ar9 A11-3b 2454 CH3 0 Aril R11-4 2416 CH3 0 Arlo R11-1 2455 CH3 0 Aril R11-5 2417 CH3 0 Arlo R11-2 2456 CH3 0 Aril R11-6 2418 CH3 0 Arlo R11-3 2457 CH3 0 Aril R11-7 2419 CH3 0 Arlo R11-4 2458 CH3 0 Aril R11-8 2420 CH3 0 Arlo R11-5 2459 CH3 0 Aril R11-9 2421 CH3 0 Arlo R11-6 2460 CH3 0 Aril R11-10 2422 CH3 0 Arlo R11-7 2461 CH3 0 Aril R11-11 2423 CH3 0 Arlo R11-8 2462 CH3 0 Aril R11-12 2424 CH3 0 Arlo R11-9 2463 CH3 0 Aril R11-13 2425 CH3 0 Arlo R11-10 2464 CH3 0 Aril R11-14 2426 CH3 0 Arlo R11-11 2465 CH3 0 Aril R11-15 2427 CH3 0 Arlo R11-12 2466 CH3 0 Aril R11-16 2428 CH3 0 Arlo R11-13 2467 CH3 0 Aril R11-17 2429 CH3 0 Arlo R11-14 2468 CH3 0 Aril R11-18 2430 CH3 0 Arlo R11-15 2469 CH3 0 Aril R11-19 2431 CH3 0 Arlo R11-16 2470 CH3 0 Aril R11-20 2432 CH3 0 Arlo R11-17 2471 CH3 0 Aril R11-21 2433 CH3 0 Arlo R11-18 2472 CH3 0 Aril R11-22 2434 CH3 0 Arlo R11-19 2473 CH3 0 Aril R11-23 2435 CH3 0 Arlo R11-20 2474 CH3 0 Aril R11-24 2436 CH3 0 Arlo R11-21 2475 CH3 0 Aril R11-25 2437 CH3 0 Arl R11-22 2476 CH3 0 Aril R11-26 2438 CH3 0 Arlo R11-23 2477 CH3 0 Aril R11-27 2439 CH3 0 Arlo R11-24 2478 CH3 0 Aril R11-28 2440 CH3 0 Arl R11-25 2479 CH3 0 Aril R11-29 2441 CH3 0 Arl R11-26 2480 CH3 0 Aril A11-la 2442 CH3 0 Arl R11-27 2481 CH3 0 Aril A11-lb 2443 CH3 0 Arlo R11-28 2482 CH3 0 Aril A11-2a 2444 CH3 0 Arl R11-29 2483 CH3 0 Aril A11-2b 2445 CH3 0 Arl A11-la 2484 CH3 0 Aril A11-3a 2446 CH3 0 Arlo A11-lb 2485 CH3 0 Aril A11-3b 2447 CH3 0 Arlo A11-2a 2486 CH3 0 Ar12 R11-1 2448 CH3 0 Arlo A11-2b 2487 CH3 0 Ar12 R11-2 2449 CH3 0 Arlo A11-3a 2488 CH3 0 Ar12 R11-3 Line R Q Ar D Line R Q Ar D
2489 CH3 0 Ar12 R11-4 2528 CI NH Arl R11-8 2490 CH3 0 Ar12 R11-5 2529 CI NH Arl R11-9 2491 CH3 0 Ar12 R11-6 2530 CI
NH Arl R11-10 2492 CH3 0 Ar12 R11-7 2531 CI
NH Arl R11-11 2493 CH3 0 Ar12 R11-8 2532 CI
NH Arl R11-12 2494 CH3 0 Ar12 R11-9 2533 CI
NH Arl R11-13 2495 CH3 0 Ar12 R11-10 2534 CI
NH Arl R11-14 2496 CH3 0 Ar12 R11-11 2535 CI
NH Arl R11-15 2497 CH3 0 Ar12 R11-12 2536 CI
NH Arl R11-16 2498 CH3 0 Ar12 R11-13 2537 CI
NH Arl R11-17 2499 CH3 0 Ar12 R11-14 2538 CI
NH Arl R11-18 2500 CH3 0 Ar12 R11-15 2539 CI
NH Arl R11-19 2501 CH3 0 Ar12 R11-16 2540 CI
NH Arl R11-20 2502 CH3 0 Ar12 R11-17 2541 CI
NH Arl R11-21 2503 CH3 0 Ar12 R11-18 2542 CI
NH Arl R11-22 2504 CH3 0 Ar12 R11-19 2543 CI
NH Arl R11-23 2505 CH3 0 Ar12 R11-20 2544 CI
NH Arl R11-24 2506 CH3 0 Ar12 R11-21 2545 CI
NH Arl R11-25 2507 CH3 0 Ar12 R11-22 2546 CI
NH Arl R11-26 2508 CH3 0 Ar12 R11-23 2547 CI
NH Arl R11-27 2509 CH3 0 Ar12 R11-24 2548 CI
NH Arl R11-28 2510 CH3 0 Ar12 R11-25 2549 CI
NH Arl R11-29 2511 CH3 0 Ar12 R11-26 2550 CI
NH Arl A11-la 2512 CH3 0 Ar12 R11-27 2551 CI
NH Arl A11-lb 2513 CH3 0 Ar12 R11-28 2552 CI
NH Arl A11-2a 2514 CH3 0 Ar12 R11-29 2553 CI
NH Arl A11-2b 2515 CH3 0 Ar12 A11-la 2554 CI NH Arl A11-3a 2516 CH3 0 Ar12 A11-lb 2555 CI NH Arl A11-3b 2517 CH3 0 Ar12 A11-2a 2556 CI NH Ar2 R11-1 2518 CH3 0 Ar12 A11-2b 2557 CI NH Ar2 R11-2 2519 CH3 0 Ar12 A11-3a 2558 CI NH Ar2 R11-3 2520 CH3 0 Ar12 A11-3b 2559 CI NH Ar2 R11-4 2521 CI NH Arl R11-1 2560 CI NH Ar2 R11-5 2522 CI NH Arl R11-2 2561 CI NH Ar2 R11-6 2523 CI NH Arl R11-3 2562 CI NH Ar2 R11-7 2524 CI NH Arl R11-4 2563 CI NH Ar2 R11-8 2525 CI NH Arl R11-5 2564 CI NH Ar2 R11-9 2526 CI NH Arl R11-6 2565 CI NH Ar2 R11-10 2527 CI NH Arl R11-7 2566 CI NH Ar2 R11-11 Line R Q Ar D Line R Q Ar D
2567 CI NH Ar2 R11-12 2606 CI NH Ar3 R11-16 2568 CI NH Ar2 R11-13 2607 Cl NH Ar3 R11-17 2569 CI NH Ar2 R11-14 2608 CI NH Ar3 R11-18 2570 CI NH Ar2 R11-15 2609 CI NH Ar3 R11-19 2571 CI NH Ar2 R11-16 2610 CI NH Ar3 R11-20 2572 CI NH Ar2 R11-17 2611 CI NH Ar3 R11-21 2573 CI NH Ar2 R11-18 2612 CI NH Ar3 R11-22 2574 CI NH Ar2 R11-19 2613 CI NH Ar3 R11-23 2575 CI NH Ar2 R11-20 2614 CI NH Ar3 R11-24 2576 CI NH Ar2 R11-21 2615 CI NH Ar3 R11-25 2577 CI NH Ar2 R11-22 2616 CI NH Ar3 R11-26 2578 CI NH Ar2 R11-23 2617 CI NH Ar3 R11-27 2579 CI NH Ar2 R11-24 2618 CI NH Ar3 R11-28 2580 CI NH Ar2 R11-25 2619 CI NH Ar3 R11-29 2581 CI NH Ar2 R11-26 2620 CI NH Ar3 A11-la 2582 CI NH Ar2 R11-27 2621 CI NH Ar3 A11-lb 2583 CI NH Ar2 R11-28 2622 CI NH Ar3 A11-2a 2584 CI NH Ar2 R11-29 2623 CI NH Ar3 A11-2b 2585 CI NH Ar2 A11-la 2624 CI NH Ar3 A11-3a 2586 CI NH Ar2 A11-lb 2625 CI NH Art A11-3b 2587 CI NH Ar2 A11-2a 2626 CI NH Art R11-1 2588 CI NH Ar2 A11-2b 2627 CI NH Art R11-2 2589 CI NH Ar2 A11-3a 2628 CI NH Art R11-3 2590 CI NH Ar2 A11-3b 2629 CI NH Art R11-4 2591 CI NH Ar3 R11-1 2630 CI NH Art R11-5 2592 CI NH Ar3 R11-2 2631 CI NH Art R11-6 2593 CI NH Ar3 R11-3 2632 CI NH AO R11-7 2594 CI NH Ar3 R11-4 2633 CI NH Art R11-8 2595 CI NH Ar3 R11-5 2634 CI NH Art R11-9 2596 CI NH Ar3 R11-6 2635 CI NH AO R11-10 2597 CI NH Ar3 R11-7 2636 CI NH AO R11-11 2598 CI NH Ar3 R11-8 2637 CI NH AO R11-12 2599 CI NH Ar3 R11-9 2638 CI NH Art R11-13 2600 CI NH Ar3 R11-10 2639 CI NH AO R11-14 2601 CI NH Ar3 R11-11 2640 CI NH AO R11-15 2602 CI NH Ar3 R11-12 2641 CI NH Art R11-16 2603 CI NH Ar3 R11-13 2642 CI NH Art R11-17 2604 CI NH Ar3 R11-14 2643 CI NH Art R11-18 2605 CI NH Ar3 R11-15 2644 CI NH Art R11-19 Line R Q Ar D Line R Q Ar D
2645 CI NH AO R11-20 2684 CI NH Ar5 R11-24 2646 CI NH AO R11-21 2685 Cl NH Ar5 R11-25 2647 CI NH Art R11-22 2686 CI NH Ar5 R11-26 2648 CI NH Art R11-23 2687 CI NH Ar5 R11-27 2649 CI NH AO R11-24 2688 CI NH Ar5 R11-28 2650 CI NH Art R11-25 2689 CI NH Ar5 R11-29 2651 CI NH Art R11-26 2690 CI NH Ar5 A11-la 2652 CI NH Art R11-27 2691 CI NH Ar5 A11-lb 2653 CI NH Art R11-28 2692 CI NH Ar5 A11-2a 2654 CI NH Art R11-29 2693 CI NH Ar5 A11-2b 2655 CI NH Art A11-la 2694 CI NH Ar5 A11-3a 2656 CI NH Art A11-1b 2695 CI NH Ar5 A11-3b 2657 CI NH Art A11-2a 2696 CI NH Ar6 R11-1 2658 CI NH Art A11-2b 2697 CI NH Ar6 R11-2 2659 CI NH Art A11-3a 2698 CI NH Ar6 R11-3 2660 CI NH Art A11-3b 2699 CI NH Ar6 R11-4 2661 CI NH Ar5 R11-1 2700 CI NH Ar6 R11-5 2662 CI NH Ar5 R11-2 2701 CI NH Ar6 R11-6 2663 CI NH Ar5 R11-3 2702 CI NH Ar6 R11-7 2664 CI NH Ar5 R11-4 2703 CI NH Ar6 R11-8 2665 CI NH Ar5 R11-5 2704 CI NH Ar6 R11-9 2666 CI NH Ar5 R11-6 2705 CI NH Ar6 R11-10 2667 CI NH Ar5 R11-7 2706 CI NH Ar6 R11-11 2668 CI NH Ar5 R11-8 2707 CI NH Ar6 R11-12 2669 CI NH Ar5 R11-9 2708 CI NH Ar6 R11-13 2670 CI NH Ar5 R11-10 2709 CI NH Ar6 R11-14 2671 CI NH Ar5 R11-11 2710 CI NH Ar6 R11-15 2672 CI NH Ar5 R11-12 2711 CI NH Ar6 R11-16 2673 CI NH Ar5 R11-13 2712 CI NH Ar6 R11-17 2674 CI NH Ar5 R11-14 2713 CI NH Ar6 R11-18 2675 CI NH Ar5 R11-15 2714 CI NH Ar6 R11-19 2676 CI NH Ar5 R11-16 2715 CI NH Ar6 R11-20 2677 CI NH Ar5 R11-17 2716 CI NH Ar6 R11-21 2678 CI NH Ar5 R11-18 2717 CI NH Ar6 R11-22 2679 CI NH Ar5 R11-19 2718 CI NH Ar6 R11-23 2680 CI NH Ar5 R11-20 2719 CI NH Ar6 R11-24 2681 CI NH Ar5 R11-21 2720 CI NH Ar6 R11-25 2682 CI NH Ar5 R11-22 2721 CI NH Ar6 R11-26 2683 CI NH Ar5 R11-23 2722 CI NH Ar6 R11-27 Line R Q Ar D Line R Q Ar D
2723 CI NH Ar6 R11-28 2762 CI NH AC A11-2a 2724 CI NH Ar6 R11-29 2763 Cl NH AC A11-2b 2725 CI NH Ar6 A11-la 2764 CI NH Ar7 A11-3a 2726 CI NH Ar6 A11-lb 2765 CI NH Ar7 A11-3b 2727 CI NH Ar6 A11-2a 2766 CI NH Ar8 R11-1 2728 CI NH Ar6 A11-2b 2767 CI NH Ar8 R11-2 2729 CI NH Ar6 A11-3a 2768 CI NH Ar8 R11-3 2730 CI NH Ar6 A11-3b 2769 CI NH Ar8 R11-4 2731 CI NH Ar7 R11-1 2770 CI NH Ar8 R11-5 2732 CI NH Ar7 R11-2 2771 CI NH Ar8 R11-6 2733 CI NH Ar7 R11-3 2772 CI NH Ar8 R11-7 2734 CI NH Ar7 R11-4 2773 CI NH Ar8 R11-8 2735 CI NH Ar7 R11-5 2774 CI NH Ar8 R11-9 2736 CI NH Ar7 R11-6 2775 CI NH Ar8 R11-10 2737 CI NH Ar7 R11-7 2776 CI NH Ar8 R11-11 2738 CI NH Ar7 R11-8 2777 CI NH Ar8 R11-12 2739 CI NH Ar7 R11-9 2778 CI NH Ar8 R11-13 2740 CI NH Ar7 R11-10 2779 CI NH Ar8 R11-14 2741 CI NH Ar7 R11-11 2780 CI NH Ar8 R11-15 2742 CI NH Ar7 R11-12 2781 CI NH Ar8 R11-16 2743 CI NH Ar7 R11-13 2782 CI NH Ar8 R11-17 2744 CI NH Ar7 R11-14 2783 CI NH Ar8 R11-18 2745 CI NH Ar7 R11-15 2784 CI NH Ar8 R11-19 2746 CI NH Ar7 R11-16 2785 CI NH Ar8 R11-20 2747 CI NH Ar7 R11-17 2786 CI NH Ar8 R11-21 2748 CI NH Ar7 R11-18 2787 CI NH Ar8 R11-22 2749 CI NH AC R11-19 2788 CI NH Ar8 R11-23 2750 CI NH Ar7 R11-20 2789 CI NH Ar8 R11-24 2751 CI NH Ar7 R11-21 2790 CI NH Ar8 R11-25 2752 CI NH AC R11-22 2791 CI NH Ar8 R11-26 2753 CI NH AC R11-23 2792 CI NH Ar8 R11-27 2754 CI NH AC R11-24 2793 CI NH Ar8 R11-28 2755 CI NH Ar7 R11-25 2794 CI NH Ar8 R11-29 2756 CI NH AC R11-26 2795 CI NH Ar8 A11-la 2757 CI NH AC R11-27 2796 CI NH Ar8 A11-1b 2758 CI NH Ar7 R11-28 2797 CI NH Ar8 A11-2a 2759 CI NH Ar7 R11-29 2798 CI NH Ar8 A11-2b 2760 CI NH Ar7 A11-la 2799 CI NH Ar8 A11-3a 2761 CI NH Ar7 A11-lb 2800 CI NH Ar8 A11-3b Line R Q Ar D Line R Q Ar D
2801 CI NH Ar9 R11-1 2840 CI NH Arl R11-5 2802 CI NH Ar9 R11-2 2841 Cl NH Arl R11-6 2803 CI NH Ar9 R11-3 2842 CI NH Arlo R11-7 2804 CI NH Ar9 R11-4 2843 CI NH Arlo R11-8 2805 CI NH Ar9 R11-5 2844 CI NH Arl R11-9 2806 CI NH Ar9 R11-6 2845 CI NH Arlo R11-10 2807 CI NH Ar9 R11-7 2846 CI NH Arlo R11-11 2808 CI NH Ar9 R11-8 2847 CI NH Arlo R11-12 2809 CI NH Ar9 R11-9 2848 CI NH Arlo R11-13 2810 CI NH Ar9 R11-10 2849 CI NH Arlo R11-14 2811 CI NH Ar9 R11-11 2850 CI NH Arlo R11-15 2812 CI NH Ar9 R11-12 2851 CI NH Arlo R11-16 2813 CI NH Ar9 R11-13 2852 CI NH Arlo R11-17 2814 CI NH Ar9 R11-14 2853 CI NH Arlo R11-18 2815 CI NH Ar9 R11-15 2854 CI NH Arlo R11-19 2816 CI NH Ar9 R11-16 2855 CI NH Arlo R11-20 2817 CI NH Ar9 R11-17 2856 CI NH Arlo R11-21 2818 CI NH Ar9 R11-18 2857 CI NH Arlo R11-22 2819 CI NH Ar9 R11-19 2858 CI NH Arlo R11-23 2820 CI NH Ar9 R11-20 2859 CI NH Arlo R11-24 2821 CI NH Ar9 R11-21 2860 CI NH Arlo R11-25 2822 CI NH Ar9 R11-22 2861 CI NH Arlo R11-26 2823 CI NH Ar9 R11-23 2862 CI NH Arlo R11-27 2824 CI NH Ar9 R11-24 2863 CI NH Arlo R11-28 2825 CI NH Ar9 R11-25 2864 CI NH Arlo R11-29 2826 CI NH Ar9 R11-26 2865 CI NH Arlo A11-la 2827 CI NH Ar9 R11-27 2866 CI NH Arl A11-lb 2828 CI NH Ar9 R11-28 2867 CI NH Arlo A11-2a 2829 CI NH Ar9 R11-29 2868 CI NH Arlo A11-2b 2830 CI NH Ar9 A11-la 2869 CI NH Arl A11-3a 2831 CI NH Ar9 A11-lb 2870 CI NH Arl A11-3b 2832 CI NH Ar9 A11-2a 2871 CI NH Aril R11-1 2833 CI NH Ar9 A11-2b 2872 CI NH Aril R11-2 2834 CI NH Ar9 A11-3a 2873 CI NH Aril R11-3 2835 CI NH Ar9 A11-3b 2874 CI NH Aril R11-4 2836 CI NH Arlo R11-1 2875 CI NH Aril R11-5 2837 CI NH Arlo R11-2 2876 CI NH Aril R11-6 2838 CI NH Arlo R11-3 2877 CI NH Aril R11-7 2839 CI NH Arlo R11-4 2878 CI NH Aril R11-8 Line R Q Ar D Line R Q Ar D
2879 CI NH Aril R11-9 2918 CI NH Ar12 R11-13 2880 CI NH Aril R11-10 2919 Cl NH Ar12 R11-14 2881 CI NH Aril R11-11 2920 CI NH Ar12 R11-15 2882 CI NH Aril R11-12 2921 CI NH Ar12 R11-16 2883 CI NH Aril R11-13 2922 CI NH Ar12 R11-17 2884 CI NH Aril R11-14 2923 CI NH Ar12 R11-18 2885 CI NH Aril R11-15 2924 CI NH Ar12 R11-19 2886 CI NH Aril R11-16 2925 CI NH Ar12 R11-20 2887 CI NH Aril R11-17 2926 CI NH Ar12 R11-21 2888 CI NH Aril R11-18 2927 CI NH Ar12 R11-22 2889 CI NH Aril R11-19 2928 CI NH Ar12 R11-23 2890 CI NH Aril R11-20 2929 CI NH Ar12 R11-24 2891 CI NH Aril R11-21 2930 CI NH Ar12 R11-25 2892 CI NH Aril R11-22 2931 CI NH Ar12 R11-26 2893 CI NH Aril R11-23 2932 CI NH Ar12 R11-27 2894 CI NH Aril R11-24 2933 CI NH Ar12 R11-28 2895 CI NH Aril R11-25 2934 CI NH Ar12 R11-29 2896 CI NH Aril R11-26 2935 CI NH Ar12 A11-la 2897 CI NH Aril R11-27 2936 CI NH Ar12 A11-lb 2898 CI NH Aril R11-28 2937 CI NH Ar12 A11-2a 2899 CI NH Aril R11-29 2938 CI NH Ar12 A11-2b 2900 CI NH Aril A11-la 2939 CI NH Ar12 A11-3a 2901 CI NH Aril A11-lb 2940 CI NH Ar12 A11-3b 2902 CI NH Aril A11-2a 2941 CI NCH3 Arl R11-1 2903 CI NH Aril A11-2b 2942 CI NCH3 Arl R11-2 2904 CI NH Aril A11-3a 2943 CI NCH3 Arl R11-3 2905 CI NH Aril A11-3b 2944 CI NCH3 Arl R11-4 2906 CI NH Ar12 R11-1 2945 CI NCH3 Arl R11-5 2907 CI NH Ar12 R11-2 2946 CI NCH3 Arl R11-6 2908 CI NH Ar12 R11-3 2947 CI NCH3 Arl R11-7 2909 CI NH Ar12 R11-4 2948 CI NCH3 Arl R11-8 2910 CI NH Ar12 R11-5 2949 CI NCH3 Arl R11-9 2911 CI NH Ar12 R11-6 2950 CI NCH3 Arl R11-10 2912 CI NH Ar12 R11-7 2951 CI NCH3 Arl R11-11 2913 CI NH Ar12 R11-8 2952 CI NCH3 Arl R11-12 2914 CI NH Ar12 R11-9 2953 CI NCH3 Arl R11-13 2915 CI NH Ar12 R11-10 2954 CI NCH3 Arl R11-14 2916 CI NH Ar12 R11-11 2955 CI NCH3 Arl R11-15 2917 CI NH Ar12 R11-12 2956 CI NCH3 Arl R11-16 Line R Q Ar D Line R Q Ar D
2957 CI NCH3 Arl R11-17 2996 CI NCH3 Ar2 R11-21 2958 CI NCH3 Arl R11-18 2997 Cl NCH3 Ar2 R11-22 2959 CI NCH3 Arl R11-19 2998 CI NCH3 Ar2 R11-23 2960 CI NCH3 Arl R11-20 2999 CI NCH3 Ar2 R11-24 2961 CI NCH3 Arl R11-21 3000 CI NCH3 Ar2 R11-25 2962 CI NCH3 Arl R11-22 3001 CI NCH3 Ar2 R11-26 2963 CI NCH3 Arl R11-23 3002 CI NCH3 Ar2 R11-27 2964 CI NCH3 Arl R11-24 3003 CI NCH3 Ar2 R11-28 2965 CI NCH3 Arl R11-25 3004 CI NCH3 Ar2 R11-29 2966 CI NCH3 Arl R11-26 3005 CI NCH3 Ar2 A11-la 2967 CI NCH3 Arl R11-27 3006 CI NCH3 Ar2 A11-lb 2968 CI NCH3 Arl R11-28 3007 CI NCH3 Ar2 A11-2a 2969 CI NCH3 Arl R11-29 3008 CI NCH3 Ar2 A11-2b 2970 CI NCH3 Arl A11-la 3009 CI NCH3 Ar2 A11-3a 2971 CI NCH3 Arl A11-lb 3010 CI NCH3 Ar2 A11-3b 2972 CI NCH3 Arl A11-2a 3011 CI NCH3 Ar3 R11-1 2973 CI NCH3 Arl A11-2b 3012 CI NCH3 Ar3 R11-2 2974 CI NCH3 Arl A11-3a 3013 CI NCH3 Ar3 R11-3 2975 CI NCH3 Arl A11-3b 3014 CI NCH3 Ar3 R11-4 2976 CI NCH3 Ar2 R11-1 3015 CI NCH3 Ar3 R11-5 2977 CI NCH3 Ar2 R11-2 3016 CI NCH3 Ar3 R11-6 2978 CI NCH3 Ar2 R11-3 3017 CI NCH3 Ar3 R11-7 2979 CI NCH3 Ar2 R11-4 3018 CI NCH3 Ar3 R11-8 2980 CI NCH3 Ar2 R11-5 3019 CI NCH3 Ar3 R11-9 2981 CI NCH3 Ar2 R11-6 3020 CI NCH3 Ar3 R11-10 2982 CI NCH3 Ar2 R11-7 3021 CI NCH3 Ar3 R11-11 2983 CI NCH3 Ar2 R11-8 3022 CI NCH3 Ar3 R11-12 2984 CI NCH3 Ar2 R11-9 3023 CI NCH3 Ar3 R11-13 2985 CI NCH3 Ar2 R11-10 3024 CI NCH3 Ar3 R11-14 2986 CI NCH3 Ar2 R11-11 3025 CI NCH3 Ar3 R11-15 2987 CI NCH3 Ar2 R11-12 3026 CI NCH3 Ar3 R11-16 2988 CI NCH3 Ar2 R11-13 3027 CI NCH3 Ar3 R11-17 2989 CI NCH3 Ar2 R11-14 3028 CI NCH3 Ar3 R11-18 2990 CI NCH3 Ar2 R11-15 3029 CI NCH3 Ar3 R11-19 2991 CI NCH3 Ar2 R11-16 3030 CI NCH3 Ar3 R11-20 2992 CI NCH3 Ar2 R11-17 3031 CI NCH3 Ar3 R11-21 2993 CI NCH3 Ar2 R11-18 3032 CI NCH3 Ar3 R11-22 2994 CI NCH3 Ar2 R11-19 3033 CI NCH3 Ar3 R11-23 2995 CI NCH3 Ar2 R11-20 3034 CI NCH3 Ar3 R11-24 Line R Q Ar D Line R Q Ar D
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3425 CI 0 Ar2 A11-la 3464 CI 0 Ar3 A11-3a 3426 CI 0 Ar2 A11-lb 3465 Cl 0 Ar4 A11-3b 3427 CI 0 Ar2 A11-2a 3466 CI 0 Ar4 R11-1 3428 CI 0 Ar2 A11-2b 3467 CI 0 Ar4 R11-2 3429 CI 0 Ar2 A11-3a 3468 CI 0 Ar4 R11-3 3430 CI 0 Ar2 A11-3b 3469 CI 0 Ar4 R11-4 3431 CI 0 Ar3 R11-1 3470 CI 0 Ar4 R11-5 3432 CI 0 Ar3 R11-2 3471 CI 0 Ar4 R11-6 3433 CI 0 Ar3 R11-3 3472 CI 0 Ar4 R11-7 3434 CI 0 Ar3 R11-4 3473 CI 0 Ar4 R11-8 3435 CI 0 Ar3 R11-5 3474 CI 0 Ar4 R11-9 3436 CI 0 Ar3 R11-6 3475 CI 0 Ar4 R11-10 3437 CI 0 Ar3 R11-7 3476 CI 0 Ar4 R11-11 3438 CI 0 Ar3 R11-8 3477 CI 0 Ar4 R11-12 3439 CI 0 Ar3 R11-9 3478 CI 0 Ar4 R11-13 3440 CI 0 Ar3 R11-10 3479 CI 0 Ar4 R11-14 3441 CI 0 Ar3 R11-11 3480 CI 0 Ar4 R11-15 3442 CI 0 Ar3 R11-12 3481 CI 0 Ar4 R11-16 3443 CI 0 Ar3 R11-13 3482 CI 0 Ar4 R11-17 3444 CI 0 Ar3 R11-14 3483 CI 0 Ar4 R11-18 3445 CI 0 Ar3 R11-15 3484 CI 0 Ar4 R11-19 3446 CI 0 Ar3 R11-16 3485 CI 0 Ar4 R11-20 3447 CI 0 Ar3 R11-17 3486 CI 0 Ar4 R11-21 3448 CI 0 Ar3 R11-18 3487 CI 0 Ar4 R11-22 3449 CI 0 Ar3 R11-19 3488 CI 0 Ar4 R11-23 3450 CI 0 Ar3 R11-20 3489 CI 0 Ar4 R11-24 3451 CI 0 Ar3 R11-21 3490 CI 0 Ar4 R11-25 3452 CI 0 Ar3 R11-22 3491 CI 0 Ar4 R11-26 3453 CI 0 Ar3 R11-23 3492 CI 0 Ar4 R11-27 3454 CI 0 Ar3 R11-24 3493 CI 0 Ar4 R11-28 3455 CI 0 Ar3 R11-25 3494 CI 0 Ar4 R11-29 3456 CI 0 Ar3 R11-26 3495 CI 0 Ar4 A11-la 3457 CI 0 Ar3 R11-27 3496 CI 0 Ar4 A11-1b 3458 CI 0 Ar3 R11-28 3497 CI 0 Ar4 A11-2a 3459 CI 0 Ar3 R11-29 3498 CI 0 Ar4 A11-2b 3460 CI 0 Ar3 A11-la 3499 CI 0 Ar4 A11-3a 3461 CI 0 Ar3 A11-1b 3500 CI 0 Ar4 A11-3b 3462 CI 0 Ar3 A11-2a 3501 CI 0 Ar5 R11-1 3463 CI 0 Ar3 A11-2b 3502 CI 0 Ar5 R11-2 Line R Q Ar D Line R Q Ar D
3503 CI 0 Ar5 R11-3 3542 CI 0 Ar6 R11-7 3504 CI 0 Ar5 R11-4 3543 Cl 0 Ar6 R11-8 3505 CI 0 Ar5 R11-5 3544 CI 0 Ar6 R11-9 3506 CI 0 Ar5 R11-6 3545 CI 0 Ar6 R11-10 3507 CI 0 Ar5 R11-7 3546 CI 0 Ar6 R11-11 3508 CI 0 Ar5 R11-8 3547 CI 0 Ar6 R11-12 3509 CI 0 Ar5 R11-9 3548 CI 0 Ar6 R11-13 3510 CI 0 Ar5 R11-10 3549 CI 0 Ar6 R11-14 3511 CI 0 Ar5 R11-11 3550 CI 0 Ar6 R11-15 3512 CI 0 Ar5 R11-12 3551 CI 0 Ar6 R11-16 3513 CI 0 Ar5 R11-13 3552 CI 0 Ar6 R11-17 3514 CI 0 Ar5 R11-14 3553 CI 0 Ar6 R11-18 3515 CI 0 Ar5 R11-15 3554 CI 0 Ar6 R11-19 3516 CI 0 Ar5 R11-16 3555 CI 0 Ar6 R11-20 3517 CI 0 Ar5 R11-17 3556 CI 0 Ar6 R11-21 3518 CI 0 Ar5 R11-18 3557 CI 0 Ar6 R11-22 3519 CI 0 Ar5 R11-19 3558 CI 0 Ar6 R11-23 3520 CI 0 Ar5 R11-20 3559 CI 0 Ar6 R11-24 3521 CI 0 Ar5 R11-21 3560 CI 0 Ar6 R11-25 3522 CI 0 Ar5 R11-22 3561 CI 0 Ar6 R11-26 3523 CI 0 Ar5 R11-23 3562 CI 0 Ar6 R11-27 3524 CI 0 Ar5 R11-24 3563 CI 0 Ar6 R11-28 3525 CI 0 Ar5 R11-25 3564 CI 0 Ar6 R11-29 3526 CI 0 Ar5 R11-26 3565 CI 0 Ar6 A11-la 3527 CI 0 Ar5 R11-27 3566 CI 0 Ar6 A11-1b 3528 CI 0 Ar5 R11-28 3567 CI 0 Ar6 A11-2a 3529 CI 0 Ar5 R11-29 3568 CI 0 Ar6 A11-2b 3530 CI 0 Ar5 A11-la 3569 CI 0 Ar6 A11-3a 3531 CI 0 Ar5 A11-1b 3570 CI 0 Ar6 A11-3b 3532 CI 0 Ar5 A11-2a 3571 CI 0 Ar7 R11-1 3533 CI 0 Ar5 A11-2b 3572 CI 0 Ar7 R11-2 3534 CI 0 Ar5 A11-3a 3573 CI 0 Ar7 R11-3 3535 CI 0 Ar5 A11-3b 3574 CI 0 Ar7 R11-4 3536 CI 0 Ar6 R11-1 3575 CI 0 Ar7 R11-5 3537 CI 0 Ar6 R11-2 3576 CI 0 Ar7 R11-6 3538 CI 0 Ar6 R11-3 3577 CI 0 Ar7 R11-7 3539 CI 0 Ar6 R11-4 3578 CI 0 Ar7 R11-8 3540 CI 0 Ar6 R11-5 3579 CI 0 Ar7 R11-9 3541 CI 0 Ar6 R11-6 3580 CI 0 Ar7 R11-10 Line R Q Ar D Line R Q Ar D
3581 CI 0 Ar7 R" -11 3620 CI 0 Ar8 R11-15 3582 CI 0 Ar7 R11-12 3621 Cl 0 Ar8 R11-16 3583 CI 0 Ar7 R11-13 3622 CI 0 Ar8 R11-17 3584 CI 0 Ar7 R11-14 3623 CI 0 Ar8 R11-18 3585 CI 0 Ar7 R11-15 3624 CI 0 Ar8 R11-19 3586 CI 0 Ar7 R11-16 3625 CI 0 Ar8 R11-20 3587 CI 0 Ar7 R11-17 3626 CI 0 Ar8 R11-21 3588 CI 0 Ar7 R11-18 3627 CI 0 Ar8 R11-22 3589 CI 0 Ar7 R11-19 3628 CI 0 Ar8 R11-23 3590 CI 0 Ar7 R11-20 3629 CI 0 Ar8 R11-24 3591 CI 0 Ar7 R11-21 3630 CI 0 Ar8 R11-25 3592 CI 0 Ar7 R11-22 3631 CI 0 Ar8 R11-26 3593 CI 0 Ar7 R11-23 3632 CI 0 Ar8 R11-27 3594 CI 0 Ar7 R11-24 3633 CI 0 Ar8 R11-28 3595 CI 0 Ar7 R11-25 3634 CI 0 Ar8 R11-29 3596 CI 0 Ar7 R11-26 3635 CI 0 Ar8 A11-la 3597 CI 0 Ar7 R11-27 3636 CI 0 Ar8 A11-lb 3598 CI 0 Ar7 R11-28 3637 CI 0 Ar8 A11-2a 3599 CI 0 Ar7 R11-29 3638 CI 0 Ar8 A11-2b 3600 CI 0 Ar7 A11-la 3639 CI 0 Ar8 A11-3a 3601 CI 0 Ar7 A11-lb 3640 CI 0 Ar8 A11-3b 3602 CI 0 Ar7 A11-2a 3641 CI 0 Ar9 R11-1 3603 CI 0 Ar7 A11-2b 3642 CI 0 Ar9 R11-2 3604 CI 0 Ar7 A11-3a 3643 CI 0 Ar9 R11-3 3605 CI 0 Ar7 A11-3b 3644 CI 0 Ar9 R11-4 3606 CI 0 Ar8 R11-1 3645 CI 0 Ar9 R11-5 3607 CI 0 Ar8 R11-2 3646 CI 0 Ar9 R11-6 3608 CI 0 Ar8 R11-3 3647 CI 0 Ar9 R11-7 3609 CI 0 Ar8 R11-4 3648 CI 0 Ar9 R11-8 3610 CI 0 Ar8 R11-5 3649 CI 0 Ar9 R11-9 3611 CI 0 Ar8 R11-6 3650 CI 0 Ar9 R11-10 3612 CI 0 Ar8 R11-7 3651 CI 0 Ar9 R11-11 3613 CI 0 Ar8 R11-8 3652 CI 0 Ar9 R11-12 3614 CI 0 Ar8 R11-9 3653 CI 0 Ar9 R11-13 3615 CI 0 Ar8 R11-10 3654 CI 0 Ar9 R11-14 3616 CI 0 Ar8 R11-11 3655 CI 0 Ar9 R11-15 3617 CI 0 Ar8 R11-12 3656 CI 0 Ar9 R11-16 3618 CI 0 Ar8 R11-13 3657 CI 0 Ar9 R11-17 3619 CI 0 Ar8 R11-14 3658 CI 0 Ar9 R11-18 Line R Q Ar D Line R Q Ar D
3659 CI 0 Ar9 R11-19 3698 CI 0 Arl R11-23 3660 CI 0 Ar9 R11-20 3699 Cl 0 Arl R11-24 3661 CI 0 Ar9 R11-21 3700 CI 0 Arlo R11-25 3662 CI 0 Ar9 R11-22 3701 CI 0 Arlo R11-26 3663 CI 0 Ar9 R11-23 3702 CI 0 Arl R11-27 3664 CI 0 Ar9 R11-24 3703 CI 0 Arlo R11-28 3665 CI 0 Ar9 R11-25 3704 CI 0 Arlo R11-29 3666 CI 0 Ar9 R11-26 3705 CI 0 Arlo A11-la 3667 CI 0 Ar9 R11-27 3706 CI 0 Arlo A11-lb 3668 CI 0 Ar9 R11-28 3707 CI 0 Arlo A11-2a 3669 CI 0 Ar9 R11-29 3708 CI 0 Arlo A11-2b 3670 CI 0 Ar9 A11-la 3709 CI 0 Arlo A11-3a 3671 CI 0 Ar9 A11-lb 3710 CI 0 Arlo A11-3b 3672 CI 0 Ar9 A11-2a 3711 CI 0 Arl 1 R11-1 3673 CI 0 Ar9 A11-2b 3712 CI 0 Arl 1 R11-2 3674 CI 0 Ar9 A11-3a 3713 CI 0 Arl 1 R11-3 3675 CI 0 Ar9 A11-3b 3714 CI 0 Arl 1 R11-4 3676 CI 0 Arlo R11-1 3715 CI 0 Arl 1 R11-5 3677 CI 0 Arlo R11-2 3716 CI 0 Arl 1 R11-6 3678 CI 0 Arlo R11-3 3717 CI 0 Arl 1 R11-7 3679 CI 0 Arlo R11-4 3718 CI 0 Arl 1 R11-8 3680 CI 0 Arlo R11-5 3719 CI 0 Arl 1 R11-9 3681 CI 0 Arlo R11-6 3720 CI 0 Arl 1 R11-10 3682 CI 0 Arlo R11-7 3721 CI 0 Arl 1 R11-11 3683 CI 0 Arlo R11-8 3722 CI 0 Arl 1 R11-12 3684 CI 0 Arlo R11-9 3723 CI 0 Arl 1 R11-13 3685 CI 0 Arl R11-10 3724 CI 0 Arl 1 R11-14 3686 CI 0 Arlo R11-11 3725 CI 0 Arl 1 R11-15 3687 CI 0 Arlo R11-12 3726 CI 0 Arl 1 R11-16 3688 CI 0 Arl R11-13 3727 CI 0 Arl 1 R11-17 3689 CI 0 Arl R11-14 3728 CI 0 Arl 1 R11-18 3690 CI 0 Arl R11-15 3729 CI 0 Arl 1 R11-19 3691 CI 0 Arlo R11-16 3730 CI 0 Arl 1 R11-20 3692 CI 0 Arl R11-17 3731 CI 0 Arl 1 R11-21 3693 CI 0 Arl R11-18 3732 CI 0 Aril R11-22 3694 CI 0 Arlo R11-19 3733 CI 0 Arl 1 R11-23 3695 CI 0 Arlo R11-20 3734 CI 0 Aril R11-24 3696 CI 0 Arlo R11-21 3735 CI 0 Arl 1 R11-25 3697 CI 0 Arlo R11-22 3736 CI 0 Arl 1 R11-26 Line R Q Ar D Line R Q Ar D
3737 CI 0 Aril R11-27 3759 CI 0 Ar12 R11-14 3738 CI 0 Aril R11-28 3760 CI 0 Ar12 R11-15 3739 CI 0 Aril R11-29 3761 CI 0 Ar12 R11-16 3740 Cl 0 Ar11 pol_la 3762 Cl 0 Ar12 R11-17 3741 Cl 0 Aril A11-lb 3763 Cl 0 Ar12 R11-18 3742 Cl 0 Ar11 18,11-2a 3764 Cl 0 Ar12 R11-19 3743 Cl 0 Ar11 18,11-2b 3765 Cl 0 Ar12 R11-20 3744 Cl 0 Ar11 18,11-3a 3766 Cl 0 Ar12 R11-21 3745 Cl 0 Ar11 18,11-3b 3767 Cl 0 Ar12 R11-22 3746 Cl 0 Ar12 R11-1 3768 Cl 0 Ar12 R11-23 3747 Cl 0 Ar12 R11-2 3769 Cl 0 Ar12 R11-24 3748 Cl 0 Ar12 R11-3 3770 Cl 0 Ar12 R11-25 3749 Cl 0 Ar12 R11-4 3771 Cl 0 Ar12 R11-26 3750 Cl 0 Ar12 R11-5 3772 Cl 0 Ar12 R11-27 3751 Cl 0 Ar12 R11-6 3773 Cl 0 Ar12 R11-28 3752 Cl 0 Ar12 R11-7 3774 Cl 0 Ar12 R11-29 3753 Cl 0 Ar12 R11-8 3775 Cl 0 Ar12 A11-la 3754 Cl 0 Ar12 R11-9 3776 Cl 0 Ar12 A11-lb 3755 Cl 0 Ar12 R11-10 3777 Cl 0 Ar12 18,11-2a 3756 Cl 0 Ar12 R11-11 3778 Cl 0 Ar12 18,11-2b 3757 Cl 0 Ar12 R11-12 3779 Cl 0 Ar12 18,11-3a 3758 Cl 0 Ar12 R11-13 3780 Cl 0 Ar12 18,11-3b As used herein, the term "compound(s) of the present invention" or "compound(s) according to the invention" refers to the compound(s) of formula (I) as defined above, which are also referred to as "compound(s) of formula l" or "compound(s) l" or "formula I compound(s)", and includes their salts, tautomers, stereoisomers, and N-oxides.
The present invention also relates to a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after. Preferred are binary mixtures of one com-pound of the present invention as component I with one mixing partner as defined herein after as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, prefera-bly from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, particularly preferably from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component ll may be used.
Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acari-cides, fungicides, herbicides, plant growth regulators, fertilizers, and the like. Preferred mixing part-ners are insecticides, nematicides and fungicides.
The following list M of pesticides, grouped and numbered according the Mode of Action Classifi-cation of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the present invention can be used and with which potential synergistic effects might be pro-duced, is intended to illustrate the possible combinations, but not to impose any limitation:
M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A
carbamates, for example al-dicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, metho-myl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1B organophosphates, for example acephate, aza-methiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, dia-zinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, etho-prophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl 0- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecar-bam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;
M.2. GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine com-pounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for exam-pie ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
M.3 Sodium channel modulators from the class of M.3A pyrethroids, for example acrinathrin, alle-thrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cyper-methrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fen-valerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluth-rin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyre-thrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and trans-fluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;
M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of M.4A
neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.2: (2E+14(6-Chloropyridin-3-yhmethylFV-nitro-2-pen-tylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yhmethy1]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; or from the class M.4B
nicotine;
M.5 Nicotinic acetylcholine receptor allosteric activators from the class of spinosyns, for example spinosad or spinetoram;
M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues as hydroprene, ki-noprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
M.8 miscellaneous non-specific (multi-site) inhibitors, for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.80 sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
M.9 Selective homopteran feeding blockers, for example M.9B pymetrozine, or M.90 flonicamid;
M.10 Mite growth inhibitors, for example M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
M.11 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacil-lus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is-raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp.
kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;
M.12 Inhibitors of mitochondria! ATP synthase, for example M.12A
diafenthiuron, or M.12B organ-otin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.120 propargite, or M.12D
tetradifon;
M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, for example chlorfenapyr, DNOC or sulfluramid;
M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for example nereistoxin ana-logues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
M.16 Inhibitors of the chitin biosynthesis type 1, as for example buprofezin;
M.17 Moulting disruptors, Dipteran, as for example cyromazine;
M.18 Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufe-nozide, halofenozide, fufenozide or chromafenozide;
M.19 Octopamin receptor agonists, as for example amitraz;
M.20 Mitochondria! complex III electron transport inhibitors, for example M.20A hydramethylnon, or M.20B acequinocyl, or M.200 fluacrypyrim;
M.21 Mitochondria! complex I electron transport inhibitors, for example M.21A
METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen-pyrad, or M.21B rotenone;
M.22 Voltage-dependent sodium channel blockers, for example M.22A indoxacarb, or M.22B met-aflumizone, or M.226.1: 242-(4-Cyanopheny1)-143-(trifluoromethyl)phenyl]ethylideneFN44-(difluo-romethoxy)phenylFhydrazinecarboxamide or M.226.2: N-(3-Chloro-2-methylpheny1)-2-[(4-chloro-phenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methyleneFhydrazinecarboxamide;
M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat;
M.24 Mitochondria! complex IV electron transport inhibitors, for example M.24A
phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
M.25 Mitochondrial complex ll electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendiamide, chlorantraniliprole (rynaxypyre), cyantraniliprole (cyazypyre), tetraniliprole, or the phthalamide compounds M.28.1: (R)-3-Chlor-N1-{2-methy1-4-[1,2,2,2 ¨tetrafluor-1-(trifluormethypethyl]pheny1}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid and M.28.2: (S)-3-Chlor-N1-{2-methy1-4-[1,2,2,2 ¨
tetrafluor-1-(trifluormethypethyl]pheny1}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, or the com-pound M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]pheny1}-1-(3-chlorpyridin-2-y1)-1H-pyrazole-5-carboxamide (proposed ISO name:
cyclaniliprole), or the com-pound M.28.4: methy1-243,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-y1)-1H-pyrazol-5-yl]carbony1}-amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; or a compound selected from M.28.5a) to M.28.5d) and M.28.5h) to M.28.51): M.28.5a) N44,6-dichloro-2-Rdiethyl-lambda-4-sulfanylidene)car-bamoy1Fphenyl]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyppyrazole-3-carboxamide; M.28.5b) N44-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyI]-6-methyl-pheny1]-2-(3-chloro-2-pyridy1)-5-(tri-fluoromethyl)pyrazole-3-carboxamide; M.28.5c) N44-chloro-2-[(di-2-propyl-lambda-4-sulfanyli-dene)carbamoyI]-6-methyl-pheny1]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5d) N44,6-dichloro-2-Rdi-2-propyl-lambda-4-sulfanylidene)carbamoy1Fphenyl]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyppyrazole-3-carboxamide; M.28.5h) N-[4,6-dibromo-2-Rdiethyl-lambda-4-sulfanylidene)carbamoy1Fphenyl]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyppyrazole-3-carboxamide;
M.28.5i) N42-(5-Amino-1,3,4-thiadiazol-2-y1)-4-chloro-6-methylpheny1]-3-bromo-1-(3-chloro-2-pyri-diny1)-1H-pyrazole-5-carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridiny1)-N42,4-dichloro-6-[[(1-cyano-1-methylethypamino]carbonyl]pheny1]-1H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)pheny1]-1-(3,5-dichloro-2-pyridy1)-1H-pyrazole-5-carboxamide;
M.28.51) N44-Chloro-2-[[(1,1-dimethylethypamino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridi-ny1)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or M.28.6: cyhalodiamide; or;
M.29. insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromo-propylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or the compounds M.29.3: 11-(4-chloro-2,6-dimethylphenyI)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, or the compound M.29.4: 3-(4'-fluoro-2,4-dimethylbipheny1-3-y1)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, or the compound M.29.5: 142-fluoro-4-methy1-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or a compound selected from the of M.29.6, wherein the compound M.29.6a) to M.29.6k): M.29.6a) (E/Z)-N41-[(6-chloro-3-pyridyl)methy1]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6b) (E/Z)-N-[14(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6c) (E/Z)-2,2,2-trifluoro-N41-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;
M.29.6d) (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyI]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6e) (E/Z)-N4141-(6-chloro-3-pyridypethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6f) (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyI]-2-pyridylidene]-2,2-difluoro-acetamide; M.29.6g) (E/Z)-2-chloro-N41-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; M.29.6h) (E/Z)-N41-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6i) (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.); M.29.6j) N41-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide; or M.29.6k) N41-[(6-chloro-3-pyridyl)methyl]-2-pyridyli-dene]-2,2,2-trifluoro-N'-isopropyl-acetamidine; or the compounds M.29.8: fluazaindolizine; or the compounds M.29.9.a): 445-(3,5-dichloropheny1)-5-(trifluoromethyl)-4H-isoxazol-3-y1]-2-methyl-N-(1-oxothietan-3-yObenzamide; or M.29.9.b): fluxametamide; or M.29.10: 5[342,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; or a compound selected from the of M.29.11, wherein the compound M.29.11b) to M.29. lip):
M.29.11.b) 3-(benzoylmethylamino)-N42-bromo-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propy1]-6-(trifluoromethyl)pheny1]-2-fluoro-benzamide; M.29.11.c) 3-(benzoylmethylamino)-2-fluoro-N42-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoromethyl)phenylFbenzamide; M.29.11.d) N43-[[[2-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoromethyl)phenyl]amino]car-bonyl]pheny1FN-methyl-benzamide; M.29.11.e) N43-[[[2-bromo-441,2,2,2-tetrafluoro-1-(trifluorome-thypethy1]-6-(trifluoromethyl)phenyl]amino]carbony1]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;
M.29.11.f) 4-fluoro-N42-fluoro-3-E2-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoro-methyl)phenyl]amino]carbonyl]pheny1FN-methyl-benzamide; M.29.11.g) 3-fluoro-N42-fluoro-3-[[[2-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoromethyl)phenyl]amino]carbonyl]pheny1]-N-methyl-benzamide; M.29.11.h) 2-chloro-N43-[[[2-iodo-441,2,2,2-tetrafluoro-1-(trifluorome-thypethy1]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenylF 3-pyridinecarboxamide; M.29.11.i) 4-cyano-N42-cyano-54[2,6-dibromo-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]car-bamoyl]phenyI]-2-methyl-benzamide; M.29.11.j) 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]pheny1]-2-fluoro-benzamide;
M.29.11.k) N454[2-chloro-6-cyano-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]car-bamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.11.I) N454[2-bromo-6-chloro-442,2,2-trifluoro-1-hydroxy-1-(trifluoromethypethyl]phenyl]carbamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.11.m) N454[2-bromo-6-chloro-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)pro-pyl]phenyl]carbamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.11.n) 4-cyano-N42-cy-ano-54[2,6-dichloro-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]pheny1]-2-methyl-benzamide; M.29.11.o) 4-cyano-N42-cyano-54[2,6-dichloro-441,2,2,2-tetrafluoro-1-(trifluo-romethypethyl]phenyl]carbamoyl]pheny1]-2-methyl-benzamide; M.29.11.p) N454[2-bromo-6-chloro-441,2,2,2-tetrafluoro-1-(trifluoromethypethyl]phenyl]carbamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or a compound selected from the of M.29.12, wherein the compound M.29.12a) to M.29.12m):
M.29.12.a) 2-(1,3-Dioxan-2-y1)-642-(3-pyridiny1)-5-thiazoly1Fpyridine;
M.29.12.b) 24642-(5-Fluoro-3-pyridiny1)-5-thiazoly1]-2-pyridiny1]-pyrimidine; M.29.12.c) 24642-(3-Pyridiny1)-5-thiazoly1]-2-pyridi-ny1]-pyrimidine; M.29.12.d) N-Methylsulfony1-642-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;
M.29.12.e) N-Methylsulfony1-642-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.29.12.f) N-Ethyl-N44-methyl-2-(3-pyridyl)thiazol-5-y1]-3-methylthio-propanamide; M.29.12.g) N-Methyl-N-[4-methyl-2-(3-pyridy0thiazol-5-y1]-3-methylthio-propanamide; M.29.12.h) N,2-Dimethyl-N44-methy1-2-(3-pyridyl)thiazol-5-y1]-3-methylthio-propanamide; M.29.12.i) N-Ethy1-2-methyl-N44-methy1-2-(3-pyridyl)thiazol-5-y1]-3-methylthio-propanamide; M.29.12.j) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN-ethyl-2-methyl-3-methylthio-propanamide; M.29.12.k) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN,2-di-methyl-3-methylthio-propanamide; M.29.12.1) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN-methyl-3-me-thylthio-propanamide; M.29.12.m) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN-ethyl-3-methylthio-pro-panamide; or the compounds M.29.14a) 1-[(6-Chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methy1-8-nitro-im-idazo[1,2-a]pyridine; or M.29.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hex-ahydroimidazo[1,2-a]pyridin-5-ol; or the compounds M.29.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1-(1,2-dimethylpropy1)-N-ethy1-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.16c) N,5-di-methyl-N-pyridazin-4-y1-1-(2,2,2-trifluoro-1-methyl-ethyppyrazole-4-carboxamide; M.29.16d) 141-(1-cyanocyclopropypethy1]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16e) N-ethyl-1-(2-fluoro-1-methyl-propy1)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16f) 1-(1,2-dimethylpropyI)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.1 6g) 141-(1-cya-nocyclopropypethy1FN,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.16h) N-methy1-1-(2-fluoro-1-methyl-propy1]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.1 6i) 1-(4,4-difluorocyclohexyl)-N-ethy1-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
or M.29.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, or M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j):
M.29.17a) N-(1-meth-ylethyl)-2-(3-pyridiny1)-2H-indazole-4-carboxamide; M.29.1 7b) N-cyclopropy1-2-(3-pyridiny1)-2H-in-dazole-4-carboxamide; M.29.17c) N-cyclohexy1-2-(3-pyridiny1)-2H-indazole-4-carboxamide;
M.29.17d) 2-(3-pyridiny1)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;
M.29. 17e) 2-(3-pyridi-nyI)-N-[(tetrahydro-2-furanyl)methy1]-2H-indazole-5-carboxamide; M.29.17f) methyl 24[2-(3-pyridi-ny1)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.29.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridiny1)-2H-indazole-5-carboxamide; M.29.1 7h) N-(2,2-difluoropropyI)-2-(3-pyridiny1)-2H-in-dazole-5-carboxamide; M.29.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carbox-amide; M.29.1 7j) N-[(5-methy1-2-pyrazinyl)methyl]-2-(3-pyridiny1)-2H-indazole-5-carboxamide, or M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d):
M.29.18a) N43-chloro-1-(3-pyridyl)pyrazol-4-y1FN-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; M.29.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-y1]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide; M.29.18c) N43-chloro-1-(3-pyridyl)pyrazol-4-y1]-3-[(2,2-difluorocyclopropyl)methylsulfany1]-N-ethyl-propana-mide; M.29.18d) N-[3-chloro-1-(3-pyridyl)pyrazol-4-y1]-3-[(2,2-difluorocyclopropyl)methylsulfiny1]-N-ethyl-propanamide; or the compound M.29.19 sarolaner, or the compound M.29.20 lotilaner.
The commercially available compounds of the M listed above may be found in The Pesticide Man-ual, 16th Edition, C. MacBean, British Crop Protection Council (2013) among other publications.
.. The online Pesticide Manual is updated regularly and is accessible through http://bcpcdata.com/pesticide-manual.html.
Another online data base for pesticides providing the ISO common names is http://www.alan-wood.net/pesticides.
The M.4 neonicotinoid cycloxaprid is known from W02010/069266 and W02011/069456, the ne-onicotinoid M.4A.2, sometimes also to be named as guadipyr, is known from W02013/003977, and the neonicotinoid M.4A.3 (approved as paichongding in China) is known from W02007/101369.
The metaflumizone analogue M.226.1 is described in CN10171577 and the analogue M.226.2 in CN102126994. The phthalamides M.28.1 and M.28.2 are both known from W02007/101540. The anthranilamide M.28.3 is described in W02005/077934. The hydrazide compound M.28.4 is de-scribed in W02007/043677. The anthranilamides M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, W02013/024009 and W02013/024010, the anthranilamide M.28.5i) is de-scribed in W02011/085575, M.28.5j) in W02008/134969, M.28.5k) in U52011/046186 and M.28.51) in W02012/034403. The diamide compound M.28.6 can be found in W02012/034472.
The spiro-ketal-substituted cyclic ketoenol derivative M.29.3 is known from W02006/089633 and the bi-phenyl-substituted spirocyclic ketoenol derivative M.29.4 from W02008/067911.
The triazoylphen-ylsulfide M.29.5 is described in W02006/043635, and biological control agents on the basis of ba-cillus firmus are described in W02009/124707. The compounds M.29.6a) to M.29.6i) listed under M.29.6 are described in W02012/029672, and M.29.6j) and M.29.6k) in W02013/129688. The ne-maticide M.29.8 is known from W02013/055584. The isoxazoline M.29.9.a) is described in W02013/050317. The isoxazoline M.29.9.b) is described in W02014/126208. The pyridalyl-type analogue M.29.10 is known from W02010/060379. The carboxamides broflanilide and M.29.11.b) to M.29.11.h) are described in W02010/018714, and the carboxamides M.29.11i) to M.29.11.p) in W02010/127926. The pyridylthiazoles M.29.12.a) to M.29.12.c) are known from W02010/006713, M.29.12.d) and M.29.12.e) are known from W02012/000896, and M.29.12.f) to M.29.12.m) from W02010/129497. The compounds M.29.14a) and M.29.14b) are known from W02007/101369.
The pyrazoles M.29.16.a) to M.29.16h) are described in W02010/034737, W02012/084670, and W02012/143317, respectively, and the pyrazoles M.29.16i) and M.29.16j) are described in US
61/891437. The pyridinylindazoles M.29.17a) to M.29.17.j) are described in W02015/038503. The pyridylpyrazoles M.29.18a) to M.29.18d) are described in U52014/0213448. The isoxazoline M.29.19 is described in W02014/036056. The isoxazoline M.29.20 is known from W02014/090918.
The following list of fungicides, in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:
A) Respiration inhibitors - Inhibitors of complex III at Q0 site (e. g. strobilurins):
azoxystrobin (A.1.1), coumethoxy-strobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), man-destrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxy.strobin (A.1.13), pyra-clostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichloropheny1)-1-methyl-allylideneaminooxymethyl)-pheny1)-2-methoxyimino-N-methyl-ac-etamide (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21), methyl-N42-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-meth-oxy-carbamate (A.1.22), 1-[3-chloro-2-[[1-(4-chloropheny1)-1H-pyrazol-3-yl]oxymethyl]pheny1]-4-me-thyl-tetrazol-5-one (A.1.23), 143-bromo-24[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]pheny1]-4-me-thyl-tetrazol-5-one (A.1.24), 1424[1-(4-chlorophenyl)pyrazol-3-yl]oxymethy1]-3-methyl-pheny1]-4-methyl-tetrazol-5-one (A.1.25), 1424[1-(4-chlorophenyl)pyrazol-3-yl]oxymethy1]-3-fluoro-pheny1]-4-methyl-tetrazol-5-one (A.1.26), 1424[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethy1]-3-fluoro-pheny1]-4-methyl-tetrazol-5-one (A.1.27), 1424[4-(4-chlorophenyl)thiazol-2-yl]oxymethy1]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.28), 143-chloro-24[4-(p-tolypthiazol-2-yl]oxymethyl]pheny1]-4-methyl-tetrazol-5-one (A.1.29), 1-[3-cyclopropy1-2-[[2-methy1-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phe-ny1]-4-methyl-tetrazol-5-one (A.1.30), 143-(difluoromethoxy)-24[2-methy1-4-(1-methylpyrazol-3-yOphenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1.31), 1-methy1-443-methy1-2-[[2-methyl-4-(1-methylpyrazol-3-y1)phenoxy]methyl]phenyl]tetrazol-5-one (A.1.32), 1-methy1-443-methy1-2-[[143-(trifluoromethyl)phenylFethylideneamino]oxymethyl]phenyl]tetrazol-5-one (A.1.33), (22E)-541-(2,4-dichlorophenyOpyrazol-3-y1Foxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2 E)-5-[1-(4-chlorophenyOpyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), (Z,2 541-(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.36), - inhibitors of complex III at Q, site: cyazofamid (A.2.1), amisulbrom (A.2.2), [(3S,6S,7R,8R)-8-benzy1-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), [(3S,6S,7R,8R)-8-benzy1-3-[[3-(acetoxymethoxy)-4-methoxy-pyri-dine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.4), [(3S,6S,7R,8R)-8-benzy1-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-me-thy1-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.5), [(3S,6S,7R,8R)-8-benzy1-34[3-(1,3-benzodioxo1-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methy1-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.6); (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)car-bonyl]amino]-6-methy1-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-y12-methylpropanoate (A.2.7), (3S,6S,7R,8R)-8-benzy1-343-[(isobutyryloxy)methoxy]-4-methoxypicolinamido]-6-methy1-4,9-dioxo-1,5-dioxonan-7-ylisobutyrate (A.2.8);
- inhibitors of complex!! (e. g. carboxamides): benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), me-pronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobipheny1-2-y1)-3-difluoromethy1-1-methy1-1H-pyrazole-4-carboxamide (A.3.19), N-(2-(1,3,3-trimethyl-buty1)-pheny1)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide (A.3.20), 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yOpyrazole-4-carboxamide (A.3.21), 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yOpy-razole-4-carboxamide (A.3.22), 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.23), 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yOpyrazole-4-carboxamide (A.3.24), 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), N-(7-fluoro-1,1,3-trimethyl-indan-4-yI)-1,3-dimethyl-pyrazole-4-carboxamide (A.3.26), N42-(2,4-dichloropheny1)-2-methoxy-1-methyl-ethy1]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide (A.3.27);
- other respiration inhibitors (e. g. complex I, uncouplers): diflumetorim (A.4.1), (5,8-difluoro-quinazolin-4-y1)-{242-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenylFethyl}-amine (A.4.2); nitro-phenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferim-zone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); and silthiofam (A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides) - 014 demethylase inhibitors (DMI fungicides): triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobu-trazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simecon-azole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 1-Vek(2S;3A)-3-(2-chloropheny1)-2-(2,4-difluoropheny1)-oxiranylmethy1]-5-thiocyanato-1H41,2,41triazolo (B.1.31), 2-Vek(2S;3R)-3-(2-chloro-pheny1)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol (B.1.32), 242-chloro-4-(4-chlorophenoxy)pheny1]-1-(1,2,4-triazol-1-y1)pentan-2-ol (B.1.33), 144-(4-chlorophenoxy)-2-(trifluoro-methyl)pheny1]-1-cyclopropy1-2-(1,2,4-triazol-1-yl)ethanol (B.1.34), 244-(4-chlorophenoxy)-2-(trifluo-romethyl)pheny1]-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.35), 242-chloro-4-(4-chlorophenoxy)pheny1]-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.36), 244-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.37), 244-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.38), 242-chloro-4-(4-chlorophenoxy)pheny1]-3-methyl-1-(1,2,4-triazol-1-y1)butan-2-ol (B.1.39), 244-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)pentan-2-01(6.1.40), 244-(4-fluorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.41), 2[2-chloro-4-(4-chlorophenoxy)pheny1]-1-(1,2,4-triazol-1-y1)pent-3-yn-2-ol (B.1.51); imid-azoles: imazalil (B.1.42), pefurazoate (B.1.43), prochloraz (B.1.44), triflumizol (B.1.45); pyrimidines, pyridines and piperazines: fenarimol (B.1.46), nuarimol (B.1.47), pyrifenox (B.1.48), triforine (B.1.49), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenypisoxazol-4-y1]-(3-pyridyl)methanol (B.1.50);
- Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox-amine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1);
C) Nucleic acid synthesis inhibitors - phenylamides or acyl amino acid fungicides: benalaxyl (0.1.1), benalaxyl-M (0.1.2), kiral-axyl (0.1.3), metalaxyl (0.1.4), metalaxyl-M (mefenoxam, 0.1.5), ofurace (0.1.6), oxadixyl (0.1.7);
- others: hymexazole (0.2.1), octhilinone (0.2.2), oxolinic acid (0.2.3), bupirimate (0.2.4), 5-fluorocytosine (0.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (0.2.6), 5-fluoro-2-(4-fluorophe-nylmethoxy)pyrimidin-4-amine (0.2.7);
D) Inhibitors of cell division and cytoskeleton - tubulin inhibitors, such as benzimidazoles, thiophanates: benomyl (D1.1), carbendazim (D1.2), fuberidazole (D1.3), thiabendazole (D1.4), thiophanate-methyl (D1.5);
triazolopyrimidines:
5-chloro-7-(4-methylpiperidin-1-y1)-6-(2,4,6-trifluoropheny1)41,2,41triazolo[1,5-a]pyrimidine (D1.6);
- other cell division inhibitors: diethofencarb (D2.1), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);
E) Inhibitors of amino acid and protein synthesis - methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
- protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydro-chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);
F) Signal transduction inhibitors - MAP! histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fenpiclonil (F.1.5), fludioxonil (F.1.6);
- G protein inhibitors: quinoxyfen (F.2.1);
G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
- lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1-(1-(4-cyano-phenyhethanesulfony1)-but-2-y1) carbamic acid-(4-fluorophenyl) ester (G.3.8);
- compounds affecting cell membrane permeability and fatty acides:
propamocarb (G.4.1);
- fatty acid amide hydrolase inhibitors: oxathiapiprolin (G.5.1), 2-{342-(1-{[3,5-bis(difluorome-thy1-1H-pyrazol-1-yl]acetyl}piperidin-4-y1)-1,3-thiazol-4-y1]-4,5-dihydro-1,2-oxazol-5-yl}phenyl me-thanesulfonate (G.5.2), 2-{342-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-y1) 1,3-thiazol-4-y1]-4,5-dihydro-1,2-oxazol-5-y1}-3-chlorophenyl methanesulfonate (G.5.3);
H) Inhibitors with Multi Site Action - inorganic active substances: Bordeaux mixture (H.1.1), copper acetate (H.1.2), copper hy-droxide (H.1.3), copper oxychloride (H.1.4), basic copper sulfate (H.1.5), sulfur (H.1.6);
- thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
- organochlorine compounds (e. g. phthalimides, sulfamides, chloronitriles): anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11), N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide (H.3.12);
- guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethy1-1H,5H41,41dithiino[2,3-c:5,6-cldipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10);
1) Cell wall synthesis inhibitors - inhibitors of glucan synthesis: validamycin (1.1.1), polyoxin B (1.1.2);
- melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);
J) Plant defence inducers - acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), potassium or sodium bicarbonate (J.1.9);
K) Unknown mode of action - bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.7), difenzoquat (K.1.8), difenzoquat-methylsulfate (K.1.9), diphenylamin (K.1.10), fenpyrazamine (K.1.11), flumetover (K.1.12), flusulfamide (K.1.13), flutianil (K.1.14), methasulfocarb (K.1.15), nitrapyrin (K.1.16), nitrothal-isopropyl (K.1.18), oxathiapiprolin (K.1.19), tolprocarb (K.1.20), oxin-copper (K.1.21), proquinazid (K.1.22), tebufloquin (K.1.23), tecloftalam (K.1.24), triazoxide (K.1.25), 2-butoxy-6-iodo-3-propylchromen-4-one (K.1.26), 243,5-bis(difluoromethyl)-1H-pyrazol-1-y1]-144-(4-{542-(prop-2-yn-1-yloxy)pheny1]-4,5-dihydro-1,2-oxazol-3-y1}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1.27), 243,5-bis(difluoromethyl)-1H-pyrazol-1-y1]-144-(4-{542-fluoro-6-(prop-2-yn-1-yloxy)pheny1]-4,5-dihydro-1,2-oxazol-3-y1}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1.28), 243,5-bis(difluoromethyl)-1H-pyrazol-1-y1]-144-(4-{542-chloro-6-(prop-2-yn-1-yloxy)pheny1]-4,5-dihydro-1,2-oxazol-3-y1}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1.29), N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-pheny1)-methyl)-2-phenyl acetamide (K.1.30), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-pheny1)-N-ethyl-N-methyl formamidine (K.1.31), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-pheny1)-N-ethyl-N-methyl formamidine (K.1.32), N'-(2-methy1-5-trifluoromethy1-4-(3-trimethylsilanyl-propoxy)-pheny1)-N-ethyl-N-methyl formamidine (K.1.33), N'-(5-difluoromethy1-2-methy1-4-(3-trimethylsilanyl-propoxy)-pheny1)-N-ethyl-N-methyl formamidine (K.1.34), methoxy-acetic acid 6-tert-buty1-8-fluoro-2,3-dimethyl-quinolin-4-ylester (K.1.35), 345-(4-methylpheny1)-2,3-dimethyl-isoxazolidin-3-y1Fpyri-dine (K.1.36), 345-(4-chloro-pheny1)-2,3-dimethyl-isoxazolidin-3-y1Fpyridine (pyrisoxazole) (K.1.37), N-(6-methoxy-pyridin-3-y1) cyclopropanecarboxylic acid amide (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-y1)-2-methy1-1H-benzoimidazole (K.1.39), 2-(4-chloro-pheny1)-N44-(3,4-dimethoxy-pheny1)-isoxazol-5-y1]-2-prop-2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-eno-ate (K.1.40), picarbutrazox (K.1.41), pentyl N46-[[(Z)-[(1-methyltetrazol-5-y1)-phenyl-methylene]ami-no]oxymethy1]-2-pyridyl]carbamate (K.1.42), 242-[(7,8-difluoro-2-methy1-3-quinolypoxy]-6-fluoro-phenyl]propan-2-ol (K.1.43), 2[2-fluoro-6-[(8-fluoro-2-methy1-3-quinolypoxy]phen-yl]propan-2-ol (K.1.44), 3-(5-fluoro-3,3,4,4-tetramethy1-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.45), 3-(4,4-difluoro-3,3-dimethy1-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.46), 3-(4,4,5-trifluoro-3,3-dimethy1-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.47), 9-fluoro-2,2-dimethy1-5-(3-quinoly1)-3H-1,4-benzoxa-zepine (K.1.48).
The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
The fungicides described by IUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A
226 917; EP-A 243 970; EP-A 256 503; EP-A 428941; EP-A 532 022; EP-A 1 028 125; EP-A
1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE
10021412;
DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO
99/24413;
WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358;
WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286;
WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 04/83193;
WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO
05/87773;
WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 11/028657, W02012/168188, WO 2007/006670, WO 2011/77514; W013/047749, WO 10/069882, WO
13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/024010 and WO 13/047441, WO 13/162072, WO 13/092224, WO
11/135833).
The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term "pesticidally effective amount" is defined below.
The compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Mono-graph No.
2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and Grube-mann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports D5243, T&F Informa, London, 2005.
Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi-ers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac-tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al-kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-ihexanol; glycols;
DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch;
fertilizers, e.g.
ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1:
Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl-sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl-inaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox-ylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Exam-pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-oxylates.
Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Exam-pies of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries.
Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports D5256, T&F
Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer-rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g.
alcohols) up to 100 wt%.
The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC) 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e. g. polyvi-nylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g.
cyclohexanone). Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC) 15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES) 5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt%
water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS) In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g.
extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with ad-dition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dis-persion or solution of the active substance.
viii) Gel (GW, GF) In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt%
thickener (e.g. car-boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub-stance.
Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME) 5-20 wt% of a compound I according to the invention are added to 5-30 wt%
organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi-cal initiator results in the formation of poly(meth)acrylate microcapsules.
Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insolu-ble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
diphenylme-thene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
The addition of a polyamine (e.g. hexamethylenediamine) results in the for-mation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS
composition.
xi) Dustable powders (DP, DS) 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
xii) Granules (GR, FG) 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
xiii) Ultra-low volume liquids (UL) 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt%
bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% col-orants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably be-tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100%
(according to NMR spectrum).
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g.
herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions com-prising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
The user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the in-vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, either individual components of the composition according to the in-vention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.
The compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
The compounds of the present invention are effective through both contact and ingestion.
Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
The compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g.
through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the present invention.
Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
As used herein, the term "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
The term "animal pest" includes arthropods, gastropods, and nematodes.
Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
The term "crop" refers to both, growing and harvested crops.
The term "plant" includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet;
fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, pumpkins, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco;
nuts, e.g. walnuts;
pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
carnation, petunias, geranium/pelargoniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane;
fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant" is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice. In plants, which have been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the genetic material of the plant. The one or more mutagenized or integrated genes are preferably selected from pat, epsps, cry1Ab, bar, cry1Fa2, cry1Ac, cry34Ab1, cry35AB1, cry3A, cryF, cry1F, mcry3a, cry2Ab2, cry3Bb1, cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asn1, and ppo5. The mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control. Of these properties, herbicide tolerance, e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance, is of particular importance. Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield oilseed rape being tolerant to imidazolinones, e.g. imazamox. Alternatively, genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady0 (glyphosate) and LibertyLinke (glufosinate).
Furthermore, insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins.
Genetically modified plants with insect resistance are commercially available under trade names including WideStrikee, Bollgarde, Agrisuree, Herculexe, YieldGardO, Genuity0, and Intactae.
Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits).
Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance. In general, all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http://www.isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CE RA)" (httplicera-gmc.org/GMCropDatabase).
It has surprisingly been found that the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
The term "plant propagation material" refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
The term "seed" embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to g per hectare, or 40 to 50 g per hectare.
The compounds of the present invention are particularly suitable for use in the treatment of seeds 40 in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
The present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the present invention. The protection of the seedling's roots and shoots is preferred.
.. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
The term "seed treatment" comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried .. out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
The present invention also comprises seeds coated with or containing the active compound. The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser .. part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, .. bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g.
tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF.
.. These formulations can be applied to the seed diluted or undiluted.
Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.
Preferably, the formulations are applied such that germination is not included.
The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 %
by weight.
In a preferred embodiment a FS formulation is used for seed treatment.
Typically, a FS
formulation may comprise 1-800 g/I of active ingredient, 1-200 g/I Surfactant, 0 to 200 g/I
antifreezing agent, 0 to 400 g/I of binder, 0 to 200 g/I of a pigment and up to 1 liter of a solvent, preferably water.
Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/I) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/I) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
The invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
The compounds of the present invention may also be used for improving the health of a plant.
Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.
As used herein "an effective and non-phytotoxic amount" means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
The terms "plant" and "plant propagation material" are defined above.
"Plant health" is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person.
The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the present invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.
As used herein, the term "non-crop insect pest" refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish-or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (e.g.
http://www.pherobase.com), and are known to those skilled in the art.
For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
Formulations of the compounds of the present invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.
The oil spray formulations differ from the aerosol recipes in that no propellants are used.
For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
The compounds of the present invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the present invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
The compounds of the present invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc.
from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
Customary application rates in the protection of materials are, for example, from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2treated material, desirably from 0.1 g to 50 g per m2.
Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
The compounds of the the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
insects from the order of Lepidoptera, for example Achroia grisella, Aclerisspp. such as A.
fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp.
such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A.
exclamation/s, A.
fucosa, A. 1;osilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophlla pometaria, Ampelophaga rubtginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota sanatoria, Antheraea pemyi, Anticarsia (=Thermesia)spp. such as A. gemmatalis; Apamea spp., Aproaerema modicella, Archt;os spp. such as A. argyrosplla, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetis mindara, Austroasca .. viridtgn:sea, Autographa gamma, Autographa nign:signa, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblast49 cactorum, Cadra cautella, Calingo brazil/ens/s, Calopas theivora, Capua reticulana, Carposina spp. such as C.
Noonenst:9, C. sasakit,".
Cephus spp., Chaetocnema andula, Cheimatobia brumata, Ch/lo spp. such as C.
lndicus, C.
suppressaks, C. partellus; Choreutt:s pariana, Chon:stoneura spp. such as C.
conflictana, C.
fumiferana, C. longicellana, C. murinana, C. occeentaks, C. rosaceana;
Chrysodebc:s (=Pseudoplusia)spp. such as C. eriosoma, C. includens; Cirpht:s unt;ouncta, Clysia ambiguella, Cnaphalocerusspp., Cnaphalocroct:s medinaks, Cnephasia spp., Cochyks hospes, Coleophora spp., Col/as eurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectaks, Cydia (=Carpocapsa)spp. such as C.
pomonella, C.
latiferreana; Dalaca noctudes, Datana integerrima, Dasychira pin/cola, Dendrolimusspp. such as D. pint, D. spectablgs, D. sibiricus; Desmia funeral/s, Diaphania spp. such as D. nit/dal/s, D.
hyalinata; Diatraea grandiosella, Diatraea saccharaks, aphthera festiva, Ear/as spp. such as E.
.. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) cur/al/s, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Ept;ohyas postvittana, Erannt:s ti/aria, Erionota thrax, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproct1:9 chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albllinea, Feltia spp. such as F.
subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G.
molesta, G. inopinata;
Halysidota spp., Harn:sina americana, Hedylepta spp., Helicoverpa spp. such as H. armigera (=Heliotht:s armigera), H. zea (=Heliotht:s zea); Heliotht:s spp. such as H.
assulta, H. sub flexa, H.
virescens; Hellula spp. such as H. undaks, H. rogataks; Helocoverpa gelotopoeon, Hemlleuca oliviae, Herpetogramma licarst:saks, Hibernia defoliaria, Hofmannophlla pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavolasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma sal/cis, Leucoptera spp. such as L. coffee//a, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrott:s alb/costa, Loxostege spp. such as L. sticticaks, L. cereraks; Lymantria spp. such as L.
dt:spar, L. monacha;
Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. such as M.
americanum, M.
californicum, M. constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. contigurata;
Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulakS, Megalopyge lanata, Melanchra picta, Melanitt:s leda, Mods spp. such as M.
lapites, M. repanda; Mods lattpes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantak:s, Nepytia spp., Nymphula spp., aketicus spp., Om/odes indicata, Ompht:sa anastomosaks, Operophtera brumata, Orgyia pseudotsugata, Oriaspp., Orthaga thyn:sak:s, Ostrinia spp. such as 0. nubilaks; Oulema oryzae, Paleacrita vemata, Panok:s flammea, Pamara spp., Papaipema nebn:s, Papilio cresphontes, Paramyelds transitella, Paranthrene regaks, Paysandt:sia archon, Pectinophora spp. such as P. gossypiella; Peridroma saucia, Perileucoptera spp., such as P. coffee//a; Phalera bucephala, Phrygandia californica, Phthorimaea spp. such as P.
operculella; Phyllocnt:stt:s citrella, Phyllonorycterspp. such as P.
blancardella, P. crataegella, P.
1:ssikit, P. ringoniella; Pien:s spp. such as P. brassicae, P. rapae, P. nap/;
Pllocrods tnpunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusaks, P.
stultana; Platyptllia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp, Plutella macukpenntS, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepgone, Pseudaletia spp. such as P. sequax, P. unipuncta; Pyrausta nubilaks, Rachtplusia nu, Richia alb/costa, Rhizobius ventraks, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festal/el/a, Scirpophaga spp. such as S. incertulas, S.
innotata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra sub flava, Sitotroga cerealella, Sparganotht:s plleriana, Spilonota lechriasp:s, S. ocellana, Spodoptera (=Lamphygma)spp. such as S.
cosmodes, S.
eridania, S. extgua, S. fruglperda, S. latt:sfascia, S. littoraltS, S. litura, S. omithogalli; Skgmellaspp., Stomopteryx subsecivella, Strymon bazochit, Sylepta derogata, Synanthedon spp.
such as S.
exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoea piiyocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T cloacella, T
pellionella; Tineola Tortrixspp. such as T viridana; Trichophaga tapetzella, Trichoplusia spp. such as T ni;
Tuta (=Scrobtpalpula) absoluta, Udea spp. such as U rubtgak:s, U rubtgaks;
Virachola spp., Yponomeuta padella, and Zeiraphera canadenst:s;
insects from the order of Coleoptera, for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. plampenntS, A. sinuatus; Agriotes spp. such as A. fuscicolks, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstiliaks, Ant:sandrus dt:spar, An/sop//a austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophoraspp. such as A. glabripennt:s; Anthonomusspp. such as A. eugenit; A.
grandt:s, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidaks, Atomaria spp. such as A. linean:s; Attagenus spp., Aulacophora femora//s, Blastophagus pimperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp.
such as B. lentis, B.
pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria flondensis, Callosobruchus chinensis, Cameraria ohndella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C. ass/mills, C. nap/; Chaetocnema tibia/is, Cleonus mendicus, Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactyl/spa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D.
undecimpunctata, D.
speciosa, D. long/corn/s. D. semOunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa arnVera, Diloboderus abderus, Diocalandra frumenti (Diocalandra skgmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestt:s, E.
vtgintioctomaculata; Epitr&spp. such as E. hirkoennt:s, E. similan:s; Eutheola humiks, Eutinobothrus brasllienst:s, Faustinus cubae, Gibbium psyllodes, Gnathocerus comutus, Hellula undaks, Heteronychus arator, Hylamorpha elegans, Hylobius abiett:s, Hylotrupes bajulus, Hypera spp. such as H.
brunnelpenntS, H. post/ca;
Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp. such as L.
bllineata, L.
melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea, Limon/us californicus, LISsorhoptrus oryzophllus, LA-us spp., Luperodes spp., Lyctus spp. such as L.
bruneus; Liogenys fuscus, Macrodactylus spp. such as M. subspinosus; Maladera matrida, Megaplatypus mutates, Megasceks spp., Melanotus communt:s, Melt:gethesspp. such as M. aeneus;
Melolontha spp. such as M. Nopocastani, M. melolontha; Metamasius hemOterus, Microtheca spp., A/kgdo/us spp. such as M. fryanus, Monochamus spp. such as M. altematus; Naupactus xanthographus, NOtus hololeucus, Oberia brevis, Oemona hirta, ayctes rhinoceros, Oryzaephllus surinamenst:s, Oryzaphagus oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. such as P.
brassicae, P.
cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha hofficola, Phyllophaga spp. such as P. hellen,- Phyllotreta spp. such as P. chrysocephala, P. nemorum, P.
striolata, P. vittula;
Phyllopertha horticola, Popillia japonica, Premnotrypesspp., Psacothea hllan:s, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopettha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R.
palmarum, R. phoenict:s, R. vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophllus spp. such as S. granaria, S. oryzae, S. zeamat:s;
Sphenophorus spp. such as S.
levt:s; Stegobium paniceum, Stemechus spp. such as S. subst:gnatus;
Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tnbolium spp.
such as T castaneum; Trogoderma spp., Tychius spp., Xylotrechusspp. such as X
pyrrhoderus;
and, Zabrus spp. such as Z tenebriodes;
insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. albopictus, A.
vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A.
gambiae, A. leucosphyrus, A. macultpenntS, A. minimus, A. quadrimaculatus, A.
sinenstS;
Bactrocera invadens, Bibio hortulanus, Calltphora erythrocephala, Calltphora vicina, Ceratitt:s capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. mace//aria;
Chrysops atlanticus, Chrysops discalis, Cho/sops sllacea, Cochliomyiaspp. such as C. hominivorax;
Contariniaspp.
such as C. sorghicola; Cordylobia anthropophaga, Culex spp. such as C.
nIgnpalpus, C. ppiens, C.
quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicodes furens, Culiseta inomata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. platura, D.
radicum; Dermatobia hominis, Drosophila spp. such as D. suzukit, Fannia spp. such as F.
canicularis; Gastraphllusspp.
such as G. intestinak:s; Geomyza tOunctata, Glossinaspp. such as G. fusapes, G. morsitans, G.
pa/pal/s. G. tachinodes; Haematobia irritans, Haplodiplost:s equestn:s, HOpelatesspp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppoboscaspp., Hydrellia phAopina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolit,-Luclliaspp. such as L. caprina, L.
cuprina, L. sericata; Lycoria pectoral/s. Mansonia tilt/Lanus, Mayetiola spp.
such as M. destructor;
Musca spp. such as M. autumnak:s, M. domestica; Muscina stabulans, Oestrus spp. such as 0.
ovt:s; Opomyza forum, Oscinellaspp. such as 0. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentOes, Phorbia spp. such as P. ant/qua, P. brassicae, P.
coarctata; Phytomyza gymnostoma, Pros/mu//urn mbdum, Ps/la rosae, Psorophora columbiae, Psorophora discolor, Rhagolett:sspp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R.
pomonella; Rivellia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidak:s; Simulium vittatum, Sitodiplost:s mosellana, Stomoxys spp. such as S. calcitrans; Tabanus spp. such as T
atratus, T bovinus, T
lineola, T simik:s; Tannia spp., Thecodtplost:s japonenstS, TOula oleracea, TOula paludosa, and Wohlfahrtiaspp;
insects from the order of Thysanoptera for example, Ballothrips biform4s, Dichromothnps corbetti, Dichromothnpsssp., Echinothnps americanus, Enneothnps flavens, Frankliniellaspp. such as F.
fusca, F occidental/s. F tritid- Heliothn;osspp., Hercinothnps femorakS, Kakothn;osspp., Microcephalothnps abdominak:s, Neohydatothnps samayunkur, Pezothnps kellyanus, RhOphorothnps cruentatus, Scirtothn;osspp. such as S. citri, S. dorsak:s, S.
perseae;
Stenchaetothnps spp, Taeniothnps cardamoni, Taeniothnps inconsequens, Thripsspp. such as T
imagines, T hawaiienst:s, T oryzae, T palmi, T parvt:spinus, T tabact,-insects from the order of Hemiptera for example, Acizzia jamatonica, Acrostemumspp. such as A.
hllare; Acyrthosipon spp. such as A. onobrycht:s, A. p:sum; Adelges laricis, Adelges tsugae, Adelphocon:sspp., such as A. rapidus, A. superbus; Aeneolamiaspp., Agonoscenaspp., Aulacon'hum solani, Aleurocanthus woglumi, Aleurodesspp., Aleurodicus disperses, Aleurolobus barodenst:s, Aleurothrbaisspp., Amrascaspp., Anasa tn:stt:s, Antestiopst:sspp., Anurapht:s cardut;
Aondiellaspp., AphanostIgma piri, Aphdula nasturtit; Aphis spp. such as A.
craccivora, A. fabae, A. forbest; A. gossypit, A. grossulariae, A. maidiradict:s, A. point; A.
sambuci, A. schneden; A.
spiraecola; Arboridia apicakS, Arilus critatus, Aspidiellaspp., Aspidiotusspp., Atanusspp., Aulacasp:s yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemt:sia spp. such as B. argentifolit, B. tabad (Aleurodes tabaci); BAssusspp. such as B. leucopterus;
Brachycaudusspp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola;
Brachycolusspp., Brachycoo/nella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C.
fulgurakS, C. pyricola .. (Psylla piri); Calk:gypona marginata, Calocon:sspp., Campylomma livida, Capitophorus horni, Cameocephala fulgida, Caveleriusspp., Ceraplastesspp., Ceratovacuna lantgera, Ceroplastes ceriferus, Cerost;oha gossypit, Chaetost;ohon fragaefoki, Chionaspis tegalenst:s, Chlorita onukit, Chromapht:s jug/and/cola, Chiysomphalus ficus, COadulina mbila, Cimexspp. such as C.
hemOterus, C. lectulanus; Coccomytllus halli, Coccus spp. such as C.
hesperdum, C.
pseudomagnollarum; Corythucha arcuata, Creontiades dllutus, Ciyptomyzus Chrysomphalus aondum, Cryptomyzus Ctenarytaina spatulata, Cyrtopeltt:s notatus, Dalbulusspp., Dasynus pOen:s, Dialeurodes spp. such as D. atrifoli4. Dalbulus maid/s, Diaphonna spp.
such as D.
spp. such as D. bromellae; Dichelops furcatus, Diconocon:s hewetti, Dora/is spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysapht:s spp. such as D.
plantaginea, D. pyri, D.
radicola; Dysaulacon'hum pseudosolant; Dysdercus spp. such as D. cingulatus, D. Intermedius;
Dysmicoccus spp., Edessa spp., Geocon:sspp., Empoasca spp. such as E. fabae, E. solana;
Epidiasp:s lepen4 Enosoma spp. such as E. lantgerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E. Integriceps; Eusceks bllobatus, Euscht:stus spp. such as E.
heros, E. impictiventn:s, E. servus; Forinia theae, Geococcus coffeae, Glycaspl:s brimblecombei, Halyomorpha spp. such as H. halys; Hellopeltt:s spp., Homa/odt:sca vitrOennt:s (=H. coagulata), Horcias nobllellus, Hyalopterus prunt; Hyperomyzus lactucae, Icerya spp. such as I. purchase; Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanodeus tloca:ssimus, Lepidosaphes spp. such as L.
ulmi; Leptocon:sa spp., Leptoglossus phyllopus, LI;oapht:s erysimi, Lygus spp.
such as L. hesperus, L. lineolan:s, L. pratenst:s; Maconellicoccus hirsutus, Marchalina he//en/ca, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrifineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanapht:s pyrarius, Melanapht:s sacchari, Melanocalks (=Tinocalks) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costa/is, Monelliopst:s pecan/s. Myzocalk:s coryli, Murgantia spp., Myzus spp. such as M.
ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia Neotoxoptera formosana, Neomegalotomus spp, Nephotett&spp. such as N. malayanus, N.
mgropictus, N.
parvus, N. virescens; Nezara spp. such as N. viridula; Nllaparvata lugens, Nysius huttoni, Oebalus spp. such as 0. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinOenntS, Parabemt:sia myricae, Parlatoria spp., Parthenolecanium spp. such as P. corni, P. persicae;
PemphIgus spp. such as P. bursar/us, P. populivenae; Peregrinus maidt:s, Perkinsiella saccharicida, Phenacoccus spp. such as P. acen:s, P. gossypit,". Phloeomyzus passerinit;
Phorodon humuk Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guldinit,".
Pinnasp:s aspidt:strae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformt:s, Psallus seriatus, Pseudacysta persea, Pseudaulacasp:s pentagona, Pseudococcus spp.
such as P. comstock4. Psylla spp. such as P. malt; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotusspp., such as Q. perniciosus; Quesada gtgas, Rastrococcus spp., Reduvius sentgs, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalost;ohum spp.
such as R. pseudobrassicas, R. insertum, R. maidt:s, R. padt,". Sagatodes spp., Sahlbergella singular/s. Sat:ssetia spp., Sappapht:s ma/a, Sappapht:s mak; Scaptocon:s spp., Scaphodes titanus, Schizapht:s graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insulan:s, Sp:sst:stllus festinus (=Stictocephala festina), Stephanitt:s nashi, Stephanitt:s pyriodes, StephanittS takeyai, Tenalaphara malayenst:s, Tetraleurodes perseae, Therioapht:s maculate, Thyanta spp. such as T accerra, T
perditor; Tibraca spp., Tomaspisspp., Toxoptera spp. such as T aurantit,".
Trialeurodes spp. such as T abuttionea, T ricini, T vaporariorum; Triatomaspp., Triozaspp., Typhlocybaspp., Unaspis spp. such as U. citri, U yanonensis; and Viteus vitifoli Insects from the order Hymenoptera for example Acanthomyops interjectus, Athalia rosae, Atta spp. such as A. captguara, A. cephalotes, A. cephalotes, A. laevtgata, A.
robusta, A. sexdens, A.
texana, Bombusspp., Brachymyrmexspp., Camponotusspp. such as C. floridanus, C.
pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogasterspp., Dasymutilla ocadentalis, aprion spp., Dolichovespula maculata, Dorymyrmexspp., Dryocosmus kunphllus, Formica spp., Hoplocampa spp. such as H. minuta, H. testudinea; Indomyrmex humllis, Lasius spp.
.. such as L. mger, Linepithema hunge, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina long/corn/s.
Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris;
Phekklespp. such as P.
megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes ruNginosa, Prenolepis impairs, Pseudomyrmex gracllis, Scheltpron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, Sinvicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphexspp., Tapinoma spp. such as T melanocephalum, T sessile; Tetramorium spp. such as T
caespitum, T
bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V squamosal;
Wasmannia auropunctata, Xylocopa sp;
Insects from the order Orthoptera for example Acheta domesticus, CallOtamus italicus, Chortoicetes terminifera, Ceuthophllusspp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllusspp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp. such as L. mt:gratoria, L. pardalina;
Melanoplus spp. such as M.
bivittatus, M. femurrubrum, M. mexicanus, M. sanguimpes, M. spretus;
Nomadacn:s septemfasciata, Oedaleus senegalenst:s, Scapten:scusspp., Scht:stocercaspp. such as S.
americana, S. gregaria, Stemopelmatusspp., Tachycines asynamorus, and Zonozerus variegatus;
Pests from the Class Arachnida for example Acari,e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A.
maculatum), Argas spp. such as A. persicu), Boophllusspp. such as B. annulatus, B. decoloratus, B. microplus, Dermacentorspp. such as D.stivarum, D. andersoni, D. variabiks, Hyalomma spp.
such as H.
truncatum, Ixodes spp. such as I. ricinus, I rubicundus, I scapulan:s, I
holocyclus, I pacificus, RhOicephalus sanguineus, Ornithodorus spp. such as 0. moubata, 0. hermsi, 0.
turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp.
such as P. ovt:s, RhOicephalusspp. such as R. sanguineus, R. appendiculatus, RhOicephalus evettsi, Rhizoglyphus spp., Sarcoptesspp. such asS. Scabiet, and Family Eriophyidae including Aceriaspp. such as A.
sheldoni, A. anthocoptes, Acallitusspp., Aculops spp. such as A. lycopersici, A. pelekassi, Aculus spp. such as A. schlechtendak. Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora;
Eriophytes nbt:s and Eriophyesspp. such as Eriophyes sheldoni, Family Tarsonemidae including Hemitarsonemusspp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki, Family Tenuipalpidae including Brevipalpus spp.
such as B.
phoenicis, Family Tetranychidae including Eotetranychusspp., Eutetranychusspp., 014g0nychu5 spp., Petrobia latens, Tetranychus spp. such as T cinnabarinus, T evansi, I
kanzawat; T, pacificus, T phaseulus, T tetanus and T urticae, Bryobia praetiosa; Panonychus spp. such as P.
ulmi, P. citri, Metatetranychus spp. and Oligonychusspp. such as 0. pratensis, a perseae, Vasates lycopersici, Raoiella id/ca, FamilyCarpoglyphidae including Carpoglyphusspp.;
Penthaleidaespp. such as Halotydeus destructor Family Demodicidae with species such as Demodexspp.; Family Trombicidea including Trombiculaspp.; Family Macronyssidae including Omothonyssusspp.; Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae;
Family Acaridae including Acarus siro; Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles reclusa;
Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root-knot nematodes, Melodogynespp. such as M. hap/a, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H.
avenae, H.
glycines, H. schachtit; H. trifoli4- Seed gall nematodes, Anguinaspp.; Stem and foliar nematodes, Aphelenchodesspp. such as A. bessey4. Sting nematodes, Belonolaimusspp. such as B.
longicaudatus; Pine nematodes, Bursaphelenchusspp. such as B. lIgnicolus, B.
xylophllus; Ring nematodes, Criconemaspp., Criconemellaspp. such as C. xenoplaxand C. omata;
and, Criconemodesspp. such as Criconemodes informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchusspp. such as D. destructor, D. dOsact,".Awl nematodes, Dolichodorusspp.;
Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophoraspp. and Hemicriconemodesspp.; Hirshmanniella spp.; Lance nematodes, Hoploaimusspp.; False rootknot nematodes, Nacobbusspp.; Needle nematodes, Longdorusspp.
such as L. elongatus; Lesion nematodes, Pratylenchusspp. such as P.
brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodey4. Burrowing nematodes, Radopholusspp.
such as R. simllis;
Rhadopholusspp.; Rhodopholusspp.;Reniform nematodes, Rotylenchusspp. such as R.
robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T
obtusus, T primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tylenchorhynchus spp. such as T claytoni, T dub/us; Citrus nematodes, Tylenchulusspp. such as T
semtpenetrans;
Dagger nematodes, Nohinema spp.; and other plant parasitic nematode species;
Insects from the order Isoptera for example Calotermes Coptotermesspp. such as C.
formosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C.
brevis, C. cavifrons; Globitermes sulfureus, Heterotermes spp. such as H.
aureus, H. longiceps, H.
tenuis; Leucotermes tiewpes, Odontotermes spp., Incisitermes spp. such as I.
minor, I Snyder Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermesspp., Procornitermesspp., Zootermopsis spp.
such as Z
angusticollis, Z nevadensis, Reticulitermesspp. such as R. hesperus, R.
tibia/is, R. speratus, R.
tiewpes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natalensis, Insects from the order Blattaria for example Blattaspp. such as B. orientalis, B. lateralis; Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Penplanetaspp.
such as P. americana, P. australasiae, P. brunnea, P. fuligginosa, P.
japonica; Supella long/pa/pa, Parcoblatta pennsylvanica, Euiycotis tloridana, Pycnoscelus surinamensis, Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephaldes spp. such as C. felts, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyllus fasciatus, Insects from the order Thysanura for example Lept:sma saccharina, Ctenolept:sma urbana, and Thermobia domestica, Pests from the class Chilopoda for example Geophllus spp., Scutigera spp. such as Scutigera coleoptrata;
Pests from the class Diplopoda for example Blaniulus guttulatus, Julusspp., Narceusspp., Pests from the class Symphyla for example Scutigerella immaculata, Insects from the order Dermaptera, for example Forticula auricularia, Insects from the order Collembola, for example Onychiurusspp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Ont:scus asellus, Porcellio scaber, Insects from the order Phthiraptera, for example Damaliniaspp., Pediculus spp.
such as Pediculus humanus capitt:s, Pediculus humanus corpon:s, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eulystemus, Haematopinus sut:s;
Linognathus spp. such as Linognathus Boy/cola bow:9, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp., Examples of further pest species which may be controlled by compounds of fomula (I) include:
from the Phylum Mollusca, class Bivalvia, for example, Dret:ssenaspp.; class Gastropoda, for example, Arlon spp., Biomphalariaspp., Bulinusspp., Derocerasspp., Galba spp., Lymnaeaspp., Oncomelania spp., Pomacea canaliclata, Succinea spp.,-from the class of the helminths, for example, Ancylostoma duodena/e, Ancylostoma ceylanicum, Acylostoma brazil/ens/s, Ancylostoma spp., Ascan:s lubricodes, Ascan:s spp., Brugia malayi, Brugia timon;
Bunostomum spp., Chabertia spp., Cionorcht:sspp., Cooperia spp., Dicrocoelium spp., Dictyocaulus fl/aria, aphyllobothrium latum, Dracunculus medinenst:s, Echinococcus granulosus, Echinococcus mu/t//ocular/s, Enterobius vermiculan:s, Faciola spp., Haemonchus spp. such as Haemonchus contortus;
Heterala:sspp., Hymenolept:s nana, Hyostrongulusspp., Loa Loa, Nematodirusspp., Oesophagostomum spp., Op:sthorcht:s spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Scht:stosomen spp., Strongylodes fuelleborni, Strongylodes stercora lis, Stronylodes spp., Taenia saginata, Taenia solium, Tr/chine/la spiraltS, Tr/chine/la nativa, Tr/chine/la britow;
Tr/chine/la nelsoni, Tr/chine/la pseudopsiraltS, Trichostrongulus spp., Trichun:s trichuria, Wuchereria bancroffil The compounds of the present invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the present invention also relates to the use of a compound of the present invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites.
Furthermore, the present invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the present invention.
The present invention also relates to the non-therapeutic use of compounds of the present invention for treating or protecting animals against infestation and infection by parasites. Moreover, the present invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the present invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the present invention.
The present invention also relates to the non-therapeutic use of compounds of the present invention for controlling or combating parasites. Moreover, the present invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
The compounds of the present invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).
Furthermore, the compounds of the present invention can be applied to any and all developmental stages.
The compounds of the present invention can be applied as such or in form of compositions comprising the compounds of the present invention.
The compounds of the present invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.
The compounds of the present invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the present invention can be systemically or non-systemically effective.
The application can be carried out prophylactically, therapeutically or non-therapeutically.
Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.
As used herein, the term "contacting" includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at its locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the present invention.
The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.
As used herein, the term "parasites" includes endo- and ectoparasites. In some embodiments of the present invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively:
fleas (Siphonaptera), e.g. Ctenocephaldes felts, Ctenocephaldes canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Penplaneta japonica, Penplaneta brunnea, Penplaneta fukgginosa, Penplaneta australasiae, and Blatta or/entails; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles macukpennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minim us, Anopheles quadrimaculatus, Calkphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops sllacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicodes furens, Culex ppiens, Culex nIgnpalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inomata, Culiseta melanura, Dermatobia hominis, Fannia caniculan:s, Gasterophllus intestinakS, Glossina morsitans, Glossina palpakS, Glossina fusapes, Glossina tachinodes, Haematobia irritans, Haplodtplost:s equestn:s, Hip elates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucllia cuprina, Lucllia sericata, Lycoria pectoral/s. Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovt:s, Phlebotomus argenttpes, Psorophora columbiae, Psorophora discolor, Prosimulium mbdum, Sarcophaga haemorrhoidak:s, Sarcophaga sp., Simulium viltatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus simik:s; lice (Phthiraptera), e.g. Pediculus humanus capitt:s, Pediculus humanus corpon:s, Pthirus pubis, Haematopinus eurystemus, Haematopinus sutS, Linognathus vituli, Boy/cola bow:9, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapulan:s, Ixodes holocyclus, Ixodes pacificus, RhIphicephalus sanguineus, Dermacentor andersoni, Dermacentor variab&s, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacot and Dermanyssus gallinae;
Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarap:s spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Ustrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemdocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (Heteropterida): Cimex lectularius, Cimex hemtpterus, Reduvius seniltS, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus,-Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g.
Trimenopon spp., Menopon spp., Trinoton spp., Boy/cola spp., Wemeckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichun:s spp., Capillaria spp.;
Rhabditida, e.g. Rhabditt:s spp., Strongylodes spp., Helicephalobus spp.;
Strongylida, e.g.
Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp.
(Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, 011ulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Mueller/us capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricodes, Ascan:s suum, Ascaridia gal/t;
Parascan:s equorum, Enterobius vermiculan:s (Threadworm), Toxocara can/s, Toxascan:s leonine, Skrjabinema spp., and Oxyun:s equ4.Camallanida, e.g. Dracunculus medinenst:s (guinea worm);
Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, apetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g.
Faciola spp., Fasciolodes magna, Paragonimus spp., Dicrocoelium spp., Fasciolopst:s buski, Clonorcht:s sinenst:s, Scht:stosoma spp., Trichobilhozia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. aphyllobothrium spp., Tenia spp., Echinococcus spp., ay//d/um caninum, Multiceps spp., Hymenolept:s spp., Mesocestodes spp., Vampirolep:s spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolept:s spp..
As used herein, the term "animal" includes warm-blooded animals (including humans) and fish.
Preferred are mammals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
Particularly preferred are domestic animals, such as dogs or cats.
In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
Generally, it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals.
For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid preparations;
- Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, .. and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.
Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
Gels are applied to or spread on the skin or introduced into body cavities.
Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.
Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.
Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.
Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
Suitable auxiliaries for this purpose are known in the art.
The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the present invention.
Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
Topical application may be conducted with compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
Generally it is favorable to apply solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
Preparation examples:
With appropriate modification of the starting materials, the procedures as described in the preparation examples below were used to obtain further compounds of formula I.
The compounds obtained in this manner are listed in the table C that follows, together with physical data.
Compounds can be characterized e.g. by coupled High Performance Liquid Chromatography /
mass spectrometry (HPLC/MS), by 1H-NMR and/or by their melting points.
Analytical HPLC - Method : Agilent Eclipse Plus C18, 50 X 4,6 mm, ID 5pm;
Elution: A = 10 mM
Amm. Formate (0.1 % Formic Acid), B = Acetonitrile (0.1 % Formic Acid), Flow =
1.2 ml/min. at 30 C; Gradient := 10% B to 100% B ¨3 min, hold for 1 min, 1 min - 10% B. Run Time = 5.01 min.
1H-NMR: The signals are characterized by chemical shift (ppm, 8 [delta]) vs.
tetramethylsilane respectively, CDCI3 for 13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplet, q = quartet, t = triplet, d = doublet and s = singlet.
Abbreviations used are: d for day(s), h for hour(s), min for minute(s), r.t./room temperature for 20 -25 C, Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, Et0Ac for ethyl acetate, THF for tetrahydrofuran, and t-BuOH for tert-butanol.
Example1: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-34244-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2- enylidene]amino]thiourea (C-1) Step 1: 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a solution of 5-bromo-2-chloro-pyrimidine (0.1 g) in N,N-Dimethyl formamide (3 mL), was added Potassium carbonate (0.142 g), Copper (I) iodide (0.01 g), 8-hydroxy quinoline (0.08 g) and 4-(trifluoromethoxy) aniline (0.11 g). The mixture was heated at 95 C for 24 h. The mixture was diluted with water (15 mL) and extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the resulting residue was subjected to flash silica gel column chromatography using a gradient of Ethyl acetate and Heptane as eluent to afford the titled compound as a off-white solid (0.05 g). LC/MS:
Rt : 1.86 min; MS: m/z = 334 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 10.12 - 9.94 (m, 1H), 8.74 - 8.56 (m, 2H), 7.89 -7.72 (m, 2H), 7.38 -7.24 (m, 2H).
Step 2: (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal:
A solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.1 g) was taken up in 1,4-Dioxane (4 mL) and water (1 mL) and the mixture degassed with nitrogen for 15 min. [1,I-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.01 g), Cesium carbonate (0.2 g) and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethy1-1,3,2-dioxaborolane (0.11 g) were added and the mixture degassed with nitrogen for an additional 10 min. The mixture was heated at 95 C for 4 h and subsequently cooled to ambient temperature. A solution of Hydrochloric acid (1 N) was added and the mixture stirred for 30 min. The mixture was neutralized with solid Sodium bicarbonate and extracted with Ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure and the residue obtained was purified by flash column chromatography eluting with a gradient of Ehyl acetate and Heptane to afford (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal as a solid (0.03 g). LC/MS: Rt :
1.65 min; MS: m/z = 324 (M+1)+; 1H NMR (300 MHz, Dmso-c) 6 10.33 (s, 1H), 9.54 (s, 1H), 8.80 (s, 2H), 8.01 -7.80 (m, 2H), 7.48 - 7.34 (m, 2H), 7.32 (s, 1H), 2.02 (s, 3H).
Step 3: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-34244-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2- enylidene]amino]thiourea A mixture of (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.130 g) in Ethanol (3 mL) was heated at 80 C for 3 h. The mixture was cooled to ambient temperature and the precipated solid was filtered and washed with cold Ethanol and n-pentane to afford the titled compound (0.2 g). LC/MS: Rt :
1.96 min; MS: m/z =
515 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.74 (s, 1H), 10.10 (s, 1H), 9.72 (s, 1H), 8.69 (s, 2H), 7.96 (s, 1H), 7.91 -7.88 (m, 2H), 7.36 - 7.19 (m, 6H), 6.69 (s, 1H), 3.14 -3.05 (m, 1H), 2.14 (s, 3H), 1.19 - 1.17 (m, 6H).
Example 2: Synthesis of 1-(2,6-dimethylpheny1)-3-[(E)-RE)-2-methyl-34244-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0-2):
A mixture of (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) and 1-amino-3-(2,6-dimethylphenyl)thiourea (0.12 g) in Ethanol (3 mL) was heated at 80 C for 3 h. The mixture was subsequently cooled to ambient temperature, the suspended solids filtered, washed sequentially with cold ethanol, pentane and dried to afford the title compound (0.2 g). LC/MS: Rt :
1.89 min; MS: m/z = 501 (M+1)+; 1H NMR (300 MHz, DMSO-a) 5 11.67 (s, 1H), 10.09 (s, 1H), 9.61 (s, 1H), 8.69 (s, 2H), 7.94 (s, 1H), 7.91 ¨ 7.80 (m, 2H), 7.42 ¨7.22 (m, 2H), 7.21 ¨7.02 (m, 3H), 6.67 (s, 1H), 2.21 (s, 3H), 2.18 (s, 6H).
Example 3: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-34244-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-3):
To a stirred solution of 1-(2-isopropylpheny1)-3-[(2-methyl-3[244-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.170 g) in Ethanol (3 mL) was added Sodium acetate (0.082 g) and Methyl bromoacetate (0.25 g). The mixture was stirred at room temperature for 30 h and subsequently diluted with water and extracted with Ethyl acetate. The organic extracts were separated, dried over anhydrous Sodium sulfate and evaporated under reduced pressure. The residue obtained was subjected to flash silica gel column chromatography eluting with a gradient of Ethylacetate-Heptane to afford the title compound as a solid (0.16 g).
LC/MS: Rt : 1.99 min; MS: m/z = 555 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 10.14 (s, 1H), 8.61 (s, 2H), 8.02 (s, 1H), 7.96 ¨ 7.78 (m, 2H), 7.57 ¨ 7.40 (m, 2H), 7.40 ¨ 7.27 (m, 3H), 7.27 ¨ 7.19 (m, 1H), 6.78 (s, 1H), 4.33 ¨ 3.99 (m, 2H), 2.85 ¨ 2.67 (m, 1H), 2.01 (s, 3H), 1.14 ¨ 1.12 (m, 6H).
Example 4: Synthesis of (2Z)-3-(2, 6-dimethylpheny1)-2-[(2-methyl-3[244-(trifluoromethoxy) anilino]pyrimidin-5-yl] prop-2-enylidene]hydrazono]thiazolidin-4-one (0-4):
A mixture of 1-(2,6-dimethylpheny1)-342-methyl-34244(trifluoromethoxy)anilino]
pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.19 g), Sodium acetate (0.094 g) and Methyl bromoacetate (0.29 g) in Ethanol (4 mL) was stirred at r.t. for 24 h. The mixture was subsequently diluted with water and extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of Ethyl acetate-Heptane to obtain the title compound (0.170 g). LC/MS: Rt : 1.95 min; MS: m/z = 541 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 10.11 (s, 1H), 8.61 (s, 2H), 8.02 (s, 1H), 7.95 ¨ 7.75 (m, 2H), 7.38 ¨ 7.28 (m, 2H), 7.28 ¨ 7.24 (m, 1H), 7.24 ¨ 7.16 (m, 2H), 6.78 (s, 1H), 4.22 (s, 2H), 2.14 (s, 3H), 2.08 (s, 6H).
Example 5: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-5):
Step 1: 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a stirred solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.1 g) in N, N-Dimethylformamide (3 mL) at 0 C was added sodium hydride (0.01 g). Methyl iodide (0.064 g) was added and the mixture stirred at r.t. for 12 h. The mixture was diluted with saturated Ammonium chloride solution, extracted with Ethyl acetate, the organic extracts dried over anhydrous Sodium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.05 g). LC/MS: Rt : 2.262 min; MS: m/z = 348 (M+1)+; 1H NMR
(300 MHz, DMS0-G) 6 8.53 (s, 2H), 7.54 ¨ 7.43 (m, 2H), 7.43 ¨ 7.32 (m, 2H), 3.44 (s, 3H), 1.20 (d, J= 19.4 Hz, 2H).
Step 2: (E)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal:
A mixture of 5-bromo-N-methyl-N[4-(trifluoromethoxy)phenyl] pyrimidin-2-amine (0.5 g) in 1,4-Dioxane (8 mL) and water (2 mL) was degassed with nitrogen gas for 15 min.
[1,1'-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.055 g), Cesium carbonate (1 g) and 2-[(E)-3, 3-diethoxyprop-1-enyI]-4, 4, 5, 5-tetramethy1-1, 3, 2-dioxaborolane (0.7 g) were added and the mixture heated at 95 C for 3 h. The reaction mixture was cooled to ambient temperature, acidified with IN HCI solution and stirred at r.t. for 30 min. The mixture was neutralized with solid Sodium bicarbonate, extracted with ethyl acetate, the organic layers dried over Sodium sulfate and evaporated under reduced pressure. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to obtain the title compound as a solid (150 mg). LC/MS: Rt : 1.98 min; MS: m/z = 324.2 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 59.59 (d, J= 7.8 Hz, 1H), 8.79 (s, 2H), 7.59 (d, J= 16.0 Hz, 1H), 7.56 ¨7.48 (m, 2H), 7.42 (d, J=
8.6 Hz, 2H), 6.84 (dd, J= 16.0, 7.8 Hz, 1H), 3.53 (s, 3H).
Step 3: 1-(2-isopropylpheny1)-34[3424N-methyl-4-(trifluoromethoxy)anilino]
pyrimidin-5-yl]prop-2-enylidene]amino]thiourea:
A mixture of (E)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.09 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.058 g) in Ethanol (3 mL) was heated at 80 C for 2 h. The mixture was subsequently cooled to ambient temperature, the suspended solids filtered and washed with cold Ethanol to afford the title compound (0.08 g). LC/MS: Rt :
1.90 min; MS: m/z =
515 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 8.64 (s, 2H), 8.00 ¨ 7.87 (m, 1H), 7.57 ¨ 7.43 (m, 2H), 7.45 ¨ 7.35 (m, 2H), 7.35 ¨ 7.29 (m, 1H), 7.29¨ 7.22 (m, 1H), 7.22 ¨ 7.12 (m, 2H), 6.99 ¨ 6.82 (m, 2H), 3.50 (s, 3H), 3.15 ¨ 2.94 (m, 1H), 1.15 (d, J= 6.9 Hz, 6H).
Step 4: (2Z)-3-(2-isopropylpheny1)-24[3424N-methyl-4-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one:
A mixture of 1-(2-isopropylpheny1)-3-[(E)-RE)-3424N-methyl-4-(trifluoromethoxy)aniline ]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.08 g), Sodium acetate (0.039 g) and Methyl bromo acetate (0.120 g) in Ethanol (3 mL) was stirred at r.t. for 12 h. The reaction mixture was subsequently diluted with water and extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the residue obtained subjected to silica gel flash column chromatograph eluting with a gradient of Ethyl acetate ¨ Heptane to afford the title compound (0.04 g). LC/MS: Rt: 1.97 min; MS: m/z = 555 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 6 8.65 (s, 2H), 8.00 (d, J= 9.3 Hz, 1H), 7.55 ¨ 7.44 (m, 4H), 7.44 ¨
7.35 (m, 2H), 7.35 ¨
7.27(m, 1H), 7.26 ¨ 7.19 (m, 1H), 7.12 ¨ 6.99 (m, 1H), 6.99 ¨ 6.85 (m, 1H), 4.29 ¨ 3.99 (m, 2H), 3.50 (s, 3H), 2.82 ¨2.64 (m, 1H), 1.21 ¨ 1.00 (m, 6H).
Example 6: Synthesis of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoro methoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (C-6):
Step 1: (E)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal A mixture of 5-bromo-N-methyl-N[4-(trifluoromethoxy) phenyl] pyrimidin-2-amine (0.4 g) in 1,4 Dioxane (6 mL) and water (1.5 mL) was degassed with nitrogen gas for 15 min.
[1,1'-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.042 g), Cesium carbonate (0.751 g) and 2-[(E)-3, 3-diethoxyprop-1-enyI]-4, 4,5, 5-tetramethy1-1, 3, 2-dioxaborolane (0.590 g) were added and the mixture heated at 95 C for 4 h. The reaction mixture was cooled to ambient temperature, acidified with IN HCI solution and stirred at r.t. for 30 min. The mixture was neutralized with solid Sodium bicarbonate, extracted with ethyl acetate, the organic layers dried over Sodium sulfate and evaporated under reduced pressure. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to obtain the title compound as a solid (0.2 g). LC/MS: Rt : 2.15 min; MS: m/z = 338.2 (M+1)+; 1H NMR (300 MHz, DMSO-a) 5 9.51 (s, 1H), 8.71 (s, 2H), 7.60 -7.47 (m, 2H), 7.47 -7.37 (m, 2H), 7.33 (s, 1H), 3.54 (s, 3H), 1.97 (s, 3H).
Step 2: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea:
A mixture of (E)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl] prop-2-enal (0.83 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.51 g) in Ethanol (6 mL) was heated at 85 C
for 3 h. The mixture was cooled to ambient temperature and the precipitated solid was filtered and washed with cold ethanol and n-pentane and dried to afford the desired product (0.850 g). LC/MS:
Rt : 2.37 min; MS: m/z = 529.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.71 (s, 1H), 9.69 (s, 1H), 8.59(s, 2H), 7.94(s, 1H), 7.53 - 7.50 (m, 2H), 7.41 -7.38 (m, 2H), 7.35 - 7.15 (m, 4H), 6.64(s, 1H), 3.52 (s, 3H), 3.14 - 3.01 (m, 1H), 2.16 (s, 3H), 1.17 (d, J= 6.9 Hz, 6H).
Example 7: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (C-7):
1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.67 g) was taken up in Ethanol (15 mL).
Ethyl-2-bromo acetate (0.97 g) and Sodium acetate (0.31 g) added and the mixture stirred a r.t. for 24 h. The reaction mixture was diluted with water and extracted with Ethyl acetate, the organic extracts dired over anhydrous Sodium sulfate and evaporated under reduced pressure. The residue obtained was purified by silica gel flash column chromatography using a gradient of Ethyl acetate and Heptane to afford the desired product. (0.59 g). LC/MS: Rt : 2.49 min; MS: m/z = 569.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.51 (s, 2H), 7.99 (s, 1H), 7.62 - 7.47 (m, 3H), 7.44 (dd, J=
8.1, 1.5 Hz, 1H), 7.42 - 7.36 (m, 2H), 7.32 (ddd, J= 8.6, 6.8, 2.0 Hz, 1H), 7.23 (dd, J= 7.9, 1.3 Hz, 1H), 6.74 (s, 1H), 4.29 - 3.95 (m, 2H), 3.51 (s, 3H), 2.84 - 2.66 (m, 1H), 2.10 (s, 3H), 1.13 (t, J= 6.3 Hz, 6H).
Example 8: Synthesis of 1-[(E)-[(E)-345-(dimethylamino)-64N-methy1-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]amino]-3-(2-isopropylphenyl)thiourea (C-8):
Step 1: Synthesis of 5-bromo-3-nitro-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine To a solution of 5-bromo-2-chloro -3-nitro pyridine (12 g, 0.050 mol) in n-butanol (100 mL) were added Triethyl amine (6.13 g, 0.060 mol) and 4-Trifluoromethoxy aniline (10.74 g, 0.060 mol). The mixture was heated at 125 C for 2 h. The mixture was subsequently cooled to ambient temperature and the precipitated solids were filtered and dried under vacuum to obtain the desired product as a brown solid (12.1 g, 63.3 % yield. LC/MS: Rt : 1.938 min; MS: m/z = 378 (M+1)+; 1H
NMR (300 MHz, DMSO-d6); 5 8.69 (d, J = 2.3 Hz, OH), 8.60 (d, J = 2.3 Hz, OH), 7.71 (d, J = 9.0 Hz, 1H), 7.37 (d, J = 8.6 Hz, 1H).
Step 2 : Synthesis of 5-bromo-N2[4-(trifluoromethoxy)phenyl]pyridine-2,3-diamine To a stirred solution of 5-bromo-3-nitro-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine (1.33 g) in Ethyl acetate (15 mL) was added Tin chloride dihydrate (3.1 g) and the mixture was heated at 80 C for 2 h. The mixture was subsequently cooled to ambient temperature and Sodium bicarbonate solution was added and the resultant mixture was filtered through a Celite bed. The organic layer was separated, washed with saturated Sodium chloride solution and water and dried over anhydrous Sodium sulphate. The organic layer was then evaporated under reduced pressure to get the desired product as a light brown solid (0.63 g, 53 % yield). LC/MS: Rt :
1.723 min; MS: m/z =
348.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 5 8.08 (s, 1H), 7.68 (d, J = 9.0 Hz, 2H), 7.52 (d, J =
2.2 Hz, 1H), 7.24 (d, J = 8.6 Hz, 2H), 7.07 (d, J = 2.2 Hz, 1H), 5.45 (s, 2H).
Step 3: Synthesis of 5-bromo-N2,N3,N3-trimethyl-N244-(trifluoromethoxy)phenyl]pyridine-2,3-diamine To a solution of 5-bromo-N2[4-(trifluoromethoxy)phenyl]pyridine-2,3-diamine (3.8 g) in N, N-Dimethyl formamide (30 mL) was added Sodium hydride, 60% suspension in mineral oil, (1 g) at 0 C and stirred for 15 minutes. Methyl iodide (7 g) was added drop-wise.The mixture was stirred at ambient temperature for 12 h and subsequently a saturated solution of Ammonium chlorde was added and the mixture extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the resultant solids subjected to flash column chromatography on Silica gel using a gradient of Ethyl acetate/Heptane as eluent to afford the desired product as a brown solid (1.33 g, 31%). LC/MS:
Rt : 2.441 min; MS:
m/z = 390.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 58.04 (d, J = 2.2 Hz, 1H), 7.51 (d, J = 2.2 Hz, 1H), 7.21 (d, J = 8.1 Hz, 1H), 6.84 (d, J = 9.1 Hz, 2H), 3.29 (s, 3H), 2.65 (s, 6H).
Step 4 : Synthesis of (E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enal A mixture of 5-bromo-N2,N3,N3-trimethyl-N244-(trifluoromethoxy)phenyl]pyridine-2,3-diamine (0.130 g) in 1,4 Dioxane (4 mL) and water (1 mL) was degassed with Nitrogen gas for 15 minutes.
[1,I-Bis(diphenylphosphino)ferrocene]palladium(11) dichloride (0.012 g), Cesium carbonate (0.217 g,) and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.171 g) were added and the mixture heated at 95 C for 4 h. IN Hydrochloric acid solution was subsequently added and the mixture was neutralized with solid Sodium bicarbonate and extracted with Ethyl acetate.The Ethyl acetate extracts were separated and filtered through Celite, dried over anhydrous Sodium sulphate and evaporated under reduced pressure. The residue obtained was subjected to Silica gel flash column chromatography using a gradient of Ethyl acetate/Heptane as eluent to afford the desired product as a pale yellow solid (0.090 g, 71 %, yield). LC/MS: Rt : 2.302 min; MS: m/z = 380.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 5 9.57 (s, 1H), 8.22 (d, J = 2.0 Hz, 1H), 7.69 - 7.39 (m, 2H), 7.29 - 7.10 (m, 2H), 6.91 (d, J = 9.1 Hz, 2H), 3.37 (s, 3H), 2.57 (s, 6H).
Step 5 : Synthesis of 1-[(E)-[(E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]amino]-3-(2-isopropylphenyhthiourea To a solution of (E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enal (0.420 g) in Ethanol (5 mL) was added 1-amino-3-(2-isopropyl phenyl)thiourea (0.231 g) and the mixture heated at 85 C for 2 h. The reaction mixture was cooled to ambient temperature and the resulting precipitate was filtered, washed with cold Ethanol and n-Pentane to get the desired product as yellow solid (0.5 g, 78.3 %, yield). LC/MS: Rt :
2.49 min; MS: m/z =
571.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 6 11.75 (s, 1H), 9.71 (s, 1H), 8.11 (d, J = 1.9 Hz, 1H), 7.98(d, J = 1.2 Hz, 1H), 7.44(d, J =2.0 Hz, 1H), 7.38 - 7.20 (m, 4H), 7.20 - 7.13 (m, 2H), 6.83(d, J = 9.3 Hz, 3H), 3.31 (s, 3H), 3.19 - 2.95 (m, 1H), 2.60(s, 6H), 2.29 -2.17 (m, 3H), 1.19 (d, J = 6.9 Hz, 6H).
Example 9: Synthesis of (2Z)-2-[(E)-[(E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy) anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]hydrazono]-3-(2-isopropylphenyhthiazolidin-4-one (C-9) To a stirred solution of 1-[(E)-[(E)-345-(dimethylamino)-64N-methy1-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]amino]-3-(2-isopropylphenyhthiourea (0.370 g) in Ethanol (5 mL) was added Sodium acetate (0.160 g) and Methyl-2-bromo acetate (0.496 g). The mixture was stirred for 12 h, Water was added and the mixture was subsequently extracted with Ethyl acetate, the organic extracts dried over anhydrous Sodium sulfate and evaporated under reduced pressure.
The residue obtained was subjected to flash column chromatography using a gradient of Ethyl acetate/Heptane as eluent to obtain the desired product as a yellow solid (0.170 g, 42 %). LC/MS:
Rt : 2.550 min; MS: m/z = 611.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 58.04 (d, J
= 2.1 Hz, 2H), 7.59 - 7.41 (m, 2H), 7.39 - 7.27 (m, 2H), 7.24 (dd, J = 7.9, 1.3 Hz, 1H), 7.16 (d, J = 8.7 Hz, 2H), 6.91 (s, 1H), 6.83(d, J = 9.1 Hz, 2H), 4.56 - 3.86 (m, 2H), 3.33(s, 4H), 2.76 (dd, J = 13.4, 6.5 Hz, 1H), 2.58 (s, 6H), 2.17 (d, J = 1.2 Hz, 3H), 1.14 (t, J = 6.9 Hz, 6H).
Example 10: Synthesis of (2E)-2-[(Z)43-(2-isopropylpheny1)-4-oxo-thiazolidin-2-ylidene]hydrazono] -N-methyl-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0-10) Step 1: 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a stirred solution of 5-bromo-2-chloro-pyrimidine (0.1 g) in N,N-Dimethylformamide (3 mL) were added Potassium carbonate (0.142 g), Copper(I)iodide (0.01 g), 8-hydroxy quinoline (0.08 g) and 4-(trifluoromethoxy) aniline (0.11 g). The mixture was heated at 95 C for 24 h, cooled to ambient temperature, diluted with Water and extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel flash column chromatography using a gradient of Ethyl acetate and Heptane as eluent to afford the desired compound as yellow solid (0.05 g, 27 % yield).
LC/MS: Rt : 1.80 min; MS: m/z = 336 (M+1)+.
Step 2: 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (2.5 g) in N, N-Dimethylformamide (10 mL) at 0 C was added Sodium Hydride (60 % dispersion in mineral oil) (0.449g) portion wise. Methyl iodide (0.7 mL) was added and the mixture stirred at ambient temperature for 12 h. The mixture was poured into ice and the precipitated solids were filtered and dried to get the desired product (2.5 g, 96 %). LC/MS: Rt : 2.25 min; MS: m/z = 348.15 (M+1)+.
Step 3: N2,N5-dimethyl-N244-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine To a solution of 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.5 g) in N-Methyl Pyrrolidone (6 mL) in a sealed tube was added Cu (I) oxide (0.021g) and a 40 % solution of Methylamine in water (6 mL). The mixture was heated at 80 C fpr 12 h and water (20 mL) followed by Ethyl acetate (20 mL) were added. The mixture was filtered through a Celite bed, the organic layer separated, dried over anhydrous Sodium sulphate and evaporated to dryness under reduced pressure. The reside was purified by Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.3 g, 70%) as a beige solid. LC/MS: Rt : 1.88 min; MS: m/z = 288.3 (M-1); 1H NMR (300 MHz, DMSO-d6) 5 7.91 (s, 2H), 7.45 - 7.33 (m, 2H), 7.33 - 7.24 (m, 2H), 5.41 (q, J = 5.3 Hz, 1H), 3.42 (s, 3H), 2.67 (d, J =
5.3 Hz, 3H).
Step 4: (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]acetic acid To a solution of 1-amino-3-(2-isopropylphenyl)thiourea (1 g) in Methanol (20 mL) was added Glyoxylic acid monohydrate (0.44 g) and the mixture stirred at ambient temperature for 2 h. The mixture was evaporated under reduced pressure and the residue was washed with n-Pentane to get the desired product (1.2g, 95 %) as a off white solid. LC/MS: Rt: 1.439 min; MS: m/z = 264 (M-1); 1H NMR (300 MHz, DMSO-d6) 5 12.34 (s, 1H), 10.32 (s, 1H), 7.44 - 7.37 (m, 2H), 7.33 (td, J =
7.8, 7.4, 1.7 Hz, 1H), 7.24 (td, J = 7.4, 1.8 Hz, 1H), 7.17 (dd, J = 7.8, 1.6 Hz, 1H), 3.05 (p, J = 6.9 .. Hz, 1H), 1.17 (d, J = 6.9 Hz, 6H).
Step 5: (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N-methyl-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide To a solution of N2,N5-dimethyl-N244-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine (0.2 g, 0.67 mmol) and (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]acetic acid (0.196 g) in Dichloromethane (20 mL) was added Diisopropylethylamine (0.25 mL) and a 50 %
solution of Propylphosphonic anhydride in Ethyl acetate (0.835g). The mixture was stirred for 12 h and subsequently poured into Water (30 mL) and extracted with Ethyl acetate (2 X
20 mL). The organic extracts were dried over anhydrous Sodium suphate and evaporated under reduced pressure and the residue obtained was subjected to Silica gel flash column chromatorgraphy eluting with a gradient of Ethyl acetate and Heptane to get the desired product ans a yellow solid (0.32 g, 87 %
yield). LC/MS: Rt: 1.178 min; MS: m/z = 546 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.77(s, 1H), 9.43 (s, 1H), 8.48 (s, 2H), 7.60 (s, 1H), 7.48 -7.27 (m, 8H), 7.27 - 7.07 (m, 4H), 3.45 (s, 5H), 3.24 (s, 5H), 2.58 - 2.50 (m, 120H), 1.13 (t, J = 6.1 Hz, 11H).
Step 6: (2E)-2-[(Z)43-(2-isopropylpheny1)-4-oxo-thiazolidin-2-ylidene]hydrazonoFN-methyl-N42-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide A mixture of (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N-methyl-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0.15 g), Sodium acetate (0.26 g, 2.75 mmol) and Methyl bromoacetate (0.11 mL) in Ethanol (20 mL) was stirred at 40 C for 12 h. The mixture was cooled to ambient temperature and Water (50 mL) was added and the mixture extracted with Ethyl acetate (2 X 50 mL). The combined organic extracts were dried over anhydrous Sodium sulphate and evaporated invacuo to a residue which was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.1 g, 62 %). LC/MS: Rt: 2.10 min; MS: m/z = 586.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.34 (s, 2H), 7.66 -7.09 (m, 9H), 4.40 -4.00 (m, 2H), 3.47 (s, 4H), 2.62 (d, J =
6.9 Hz, 1H), 1.03 (dd, J
.. = 22.9, 6.8 Hz, 6H).
Example 11: Synthesis of (2E)-2-[(Z)43-(2-isopropylpheny1)-4-oxo-thiazolidin-2-ylidene]hydrazonoFN424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (C-11) A mixture of (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0.1 g, 0.188 mmol), Sodium acetate (0.154 g) and Methyl bromoacetate (0.076 mL) was taken up in Ethanol (20 mL) and stirred at 40 C for 12 h.
The mixture was cooled to ambient temperature and Water (50 mL) was added and extracted with Ethyl acetate ( 2 X 50 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the resultant residue was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.05 g, 46%). LC/MS: Rt: 2.149 min; MS: m/z = 572.3 (M+1)+;
1H NMR (300 MHz, DMSO-d6) 5 10.36 (s, 1H), 8.66 (s, 2H), 7.67 (s, 1H), 7.49 (d, J = 9.0 Hz, 3H), 7.37 (d, J = 8.4 Hz, 3H), 7.26 (dd, J = 7.9, 1.4 Hz, 1H), 4.51 -3.98 (m, 2H), 3.48 (s, 3H), 1.13 (dd, J = 6.9, 4.4 Hz, 6H).
Example 12: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-346-[N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-12) Step 1: Synthesis of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine A mixture of 2-amino-5-bromo pyridine (4.4 g), Copper (II) acetate (10.85 g) and Potassium phosphate (6.128 g) in Dimethylsulfoxide (70 mL) was heated at 100 C for 24 h. The mixture was subsequently cooled to ambient temperature, Ethyl acetate was added and the mixture filtered through Celite. The organic layer was separated, washed with saturated Sodium chloride solution, Water and subsequently dried over anhydrous Sodium sulphate. The organic layer was then evaporated invacuo and the residue subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to afford the desired product as a brown solid. (2.3 g, 27 %). LC/MS: Rt : 2.139 min; MS: m/z = 335.30 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.29 (d, J = 2.5 Hz, 1H), 7.79 (d, J = 9.1 Hz, 2H), 7.48 - 7.14 (m, 2H), 6.88 (dd, J =
8.9, 1.4 Hz, 2H).
Step 2: Synthesis of 5-bromo-N-methyl-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine To a 0 C solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine (2.3 g) in N, N-Dimethyl formamide (15 mL) was added Sodium hydride (0.2 g). Methyl iodide (1.47 g) was added drop-wise and the mixture stirred at ambient temperature for 12 h. Saturated Ammonium chloride solution was added and the mixture extracted with Ethyl acetate and the extract was dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to get the desired product as a off-white solid (1.75 g, 73 %). LC/MS: Rt: 2.209 min;
MS: m/z = 349.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 58.23 (d, J = 2.5 Hz, 1H), 7.65 (dt, J =
9.1, 2.0 Hz, 1H), 7.43 (s, 4H), 6.58 (d, J = 9.1 Hz, 1H), 3.37 (s, 3H).
Step 3: Synthesis of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal A mixture of 5-bromo-N-methyl-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine (1.75 g, 5.05 mmol), 1,4 Dioxane (20 mL) and Water (5 mL) was degassed with nitrogen gas. [1,1'-Bis(diphenyl phosphino)ferrocene]palladium(II) dichloride (0.370 g), Cesium carbonate (3.3 g) and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethy1-1,3,2-dioxaborolane (2.59 g) were added and the degassing continued for a further 10 min. The mixture was heated at 90 C
for 3 h and cooled to ambient temperature. 1N Hydrochloric acid solution was added and the mixture was neutralized with solid Sodium bicarbonate. The mixture was extracted with Ethyl acetate and the extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the resultant residue was subjected to Silica gel flash chromatography eluting with a Ethyl acetate/Heptane gradient to get the desired compound as a white solid solid (1.2 g, 71 %). LC/MS: Rt : 2.170 min; MS: m/z = 337.2 (M+1); 1H NMR (300 MHz, DMSO-d6) 5 9.49 (s, 1H), 8.47 (d, J = 2.4 Hz, 1H), 7.84 (dd, J = 9.1, 2.5 Hz, 1H), 7.61 ¨7.41 (m, 4H), 7.37 (s,1H), 6.66 (d, J = 9.0 Hz, 1H), 3.47 (s, 3H), 1.97 (d, J = 1.1 Hz, 3H).
Step 4: Synthesis of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]-3-pyridyl]prop-2-enylidene]amino]thiourea To a stirred solution of (E)-2-methy1-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal (0.350 g) in Ethanol (4 mL) was added 1-amino-3-(2-isopropylphenyl)thiourea (0.217 g) and the mixture heated at 85 C for 3 h. Water was added and the mixture was extracted with ethyl acetate, the extracts dried over anhydrous Sodium sulphate, evaporated and the residue was flash chromatographed over Silica gel to get the desired product as a yellow solid (0.22 g, 40 %). LC/MS:
Rt : 2.423 min; MS: m/z = 528.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.68 (s, 1H), 9.66 (s, 1H), 8.37 ¨ 8.25 (m, 1H), 7.94 (s, 1H), 7.77 ¨7.62 (m, 1H), 7.52 ¨ 7.38 (m, 5H), 7.44 ¨ 7.26 (m, 2H), 7.27(s, 1H), 7.26 ¨ 7.10 (m, 1H), 6.72 ¨ 6.61 (m, 2H), 4.03(q, J = 7.1 Hz, 1H), 3.44(s, 4H), 3.09 (p, J = 6.8 Hz, 1H), 2.16 (s, 3H), 1.99 (s, 1H), 1.18 (d, J = 6.9 Hz, 6H).
Step 5: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enylidene]hydrazono]thiazolidin-4-one To a stirred solution of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]-3-pyridyl]prop-2-enylidene]amino]thiourea (0.175 g) in Ethanol ( 4 mL) were added sodium acetate (0.082 g), and Methyl-2-bromo acetate (0.25 g) and the mixture stirred for 16 h. The mixture was subsequently diluted with Water and extracted with Ethyl acetate, the extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure to get a residue which was flash chromatographed to ger the desired product as yellow solid (0.08 g, 40 %, yield). LC/MS: Rt : 2.465 min; MS: m/z = 568.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.26 (d, J = 2.3 Hz, 1H), 7.99 (s, 1H), 7.64 (dd, J = 9.0, 2.4 Hz, 1H), 7.55 ¨
7.38 (m, 6H), 7.32 (ddd, J = 8.6, 6.8, 2.0 Hz, 1H), 7.23 (dd, J = 7.9, 1.4 Hz, 1H), 6.80 (s, 1H), 6.64 (d, J = 8.9 Hz, 1H), 4.20 (d, J = 17.4 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.43 (s, 3H), 2.76 (p, J =
6.6 Hz, 1H), 2.14 ¨ 2.07 (m, 3H), 1.13 (t, J = 6.4 Hz, 6H).
Example 13: Synthesis of (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0-13) Step 1: N2-methyl-N2[4-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine To a solution of 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (1g) in N-Methylpyrrolidone (10 mL) in a sealed tube was added Copper (1) oxide (0.041 g) and a 30 %
solution of Methyl amine in water (10 mL). The mixture was heated at 80 C for 12 h. Water (20 mL) and Ethyl acetate (20 mL) were added and the mixture filtered through Celite.
The organic layer was separated, washed with a saturated solution of Sodium chloride, dried over anhydrous Sodium sulphate and evaporated invacuo. The residue obtained was subjected to Silica gel flash column chromatography using a Ethyl acetate/Heptane gradient to obtain the desired product (0.7 g, 85 %) as a beige solid. LC/MS: Rt: 1.715 min; MS: m/z = 285.2 (M-1).
Step-2: (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N424N-methyl-4-(trifluoromethoxy) anilino]pyrimidin-5-yl]acetamide To a solution of N2-methyl-N2[4-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine (0.1 g) and (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]acetic acid (0.10 g) in Dichloromethane (10 mL) was added Diisopropylethylamine (0.125 mL) and a 50 % solution of Propylphosphonic anhydride solution (0.45 g). The mixture was stirred at ambient temperature for 12 h. Water (30 mL) was added and the mixture extracted with Ethyl acetate (2 X 20 mL). The organic extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the resultant residue was subjected to Silica gel flash column chromatography to get the desired product (0.32g, 87 %) as a yellow solid. LC/MS: Rt : 2.134 min; MS: m/z = 532 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 5 12.29 (s, 1H), 10.36 (s, 1H), 10.13 (s, 1H), 8.55 (s, 2H), 7.56 - 7.45 (m, 3H), 7.45 - 7.34 (m, 4H), 7.26 (dtd, J = 22.5, 8.5, 7.8, 1.7 Hz, 2H), 3.48 (s, 3H), 3.07 (p, J =
6.8 Hz, 1H), 1.19 (d, J = 6.9 Hz, 6H).
Example 14: Synthesis of 1-(2-isopropylpheny1)-3-[(E)(E)-3424N-methyl-4-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]imidazolidine-2,4-dione (0-14) A mixture of (E)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.135 g), 3-amino-1-(2-isopropylphenyl)imidazolidine-2,4-dione (0.097g) and Concentrated Hydrochloric acid .. (2 drops) in Ethanol was heated at 80 C for 3 h. The mixture was cooled to ambient temperature and the precipitated solids were filtered and washed with cold ethanol and dried under vacuum to afford the desired product as a beige colored solid. (0.064 g, 28%). LC/MS: Rt : 2.180 min; MS: m/z = 539 (M+1)+.
Example 15: Synthesis of 1-(2-isopropylpheny1)-3-[(E)-[(E)-2-methy1-3-[6-[N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enylidene]amino]thiourea (C-15) A mixture of (E)-2-methy1-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal (0.32 g) and 1-amino-3-(2-isopropylphenyl)thiourea ( 0.217 g) in Ethanol (5 mL) was heated at 85 C for 3 h. The mixture was cooled to ambient temperature, diluted with water, extracted with Ethyl acetate and the extracts were dried over anhydrous Sodium sulphate and evaporated invacuo. The residue obtained was subjected to flash column chromatography using a gradient of Ethyl acetate and heptane as eluent to afford the desired product as a yellow solid (0.26 g, 46 %). LC/MS: Rt:
2.39 min; MS: m/z = 528.7 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.70 (s, 1H), 9.68 (s, 1H), 8.31 (d, J = 2.3 Hz, 2H), 7.94 (s, 1H), 7.81 (dd, J = 9.2, 2.4 Hz, 2H), 7.59 -7.14 (m, 12H), 6.72 (d, J
= 8.5 Hz, 3H), 3.09 (p, J = 6.8 Hz, 1H), 2.16 (s, 3H), 1.18 (d, J = 6.8 Hz, 7H).
Example 16: Synthesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-344-methyl-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0-16) Step 1: 5-bromo-2-chloro-4-methyl-pyrimidine A mixture of 5-Bromo 2,4-dichloropyrimidine (0.4 g) and Iron(111)acetylacetonate (0.062 g) in Tetrahydrofuran (10 mL) was cooled to 0 C. Methyl magnessium bromide (3 M
solution in Diethyl ether) (0.76 mL) was added dropwise and the mixture stirred for 2 h. Saturated Ammonium Chloride solution was added and the mixture extracted with Ethyl acetate (2 X
20 mL). The organic extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure to get a residue which was purified by Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and n-heptane to afford the desired product (0.220 g, 60 %) as a white solid. 1H
NMR (300 MHz, 0D0I3) 5 8.52 (s, 1H), 2.57 (s, 3H).
Step 2: 5-bromo-4-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine A mixture of 5-bromo-2-chloro-4-methyl-pyrimidine (2 g), 4-Trifluoromethoxyaniline (2.04 g), concentrated Hydrochloric acid solution (0.2 mL) in in 2-propanol (20 mL) was heated at 100 C for 4 h. The mixture was subsequently cooled to room temperature, poured into ice and basified with a saturated solution Sodium bicarbonate solution and precipitated solids were filtered. The filtered solid was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and n-Heptane to afford the desired product (1.75 g, 52 %) as an off-white solid. LC/MS:
Rt: 2.20 min; MS: m/z = 346.1 (M-1); 1H NMR (300 MHz, 0D0I3) 5 8.32 (s, 1H), 7.88 (s, 1H), 7.63 -7.51 (m, 2H), 7.19 -7.07 (m, 2H), 2.50 (s, 3H).
Step 3: 5-bromo-N,4-dimethyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To the solution of 5-bromo-4-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (1.5 g) in N, N-Dimethylformamide (30 mL) at 0 C was added Sodium hydride (60% dispersion in mineral oil) (0.207g) portion wise. Methyl iodide (0.35 mL) was added and the mixture stirred at 0 C for 1 h.
The reaction mixture was poured into ice and extracted with Ethyl acetate (2 X
20 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the residue subjected to Silica gel flash column chromatography using a gradient of Ethyl acetate and n-heptane as eluent to get the desired product to get the desired product (1.4 g, 89 % yield) as a beige solid. LC/MS: Rt : 2.388 min; MS: m/z = 364.3 (M+1)+;
1H NMR (300 MHz, 0D0I3) 5 8.20 (s, 1H), 7.27 (d, J = 9.0 Hz, 2H), 7.17 (d, J = 8.1 Hz, 2H), 3.47 (d, J = 1.3 Hz, 3H), 2.40 (d, J = 7.0 Hz, 3H).
Step 4: (E)-2-methy1-344-methy1-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal A mixture of 5-bromo-N,4-dimethyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.25 g), Cesium carbonate (0.45 g) and 2-[(Z)-3,3-diethoxy-1-methyl-prop-1-eny1]-4,4,5,5-tetramethy1-1,3,2-dioxaborolane (0.28 g) in 1,4-Dioxane (12 mL) and water (3 mL) was degassed for 10 min, followed by the addition of [1,I-Bis(diphenylphosphino)ferrocene] palladium(II) dichloride (0.05 g) and the mixture heated at 90 C for 2 h. The mixture was subsequently cooled to ambient temperature and water (10 mL) was added and the mixture extracted with Ethyl acetate (20 mL).
The Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the residue obtained was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate/n-Heptane to afford the desired product (0.2 4g, 99 %) as an off white solid. Rt :2.173 min; MS: m/z = 352.4 (M+1)+; 1H NMR (300 MHz, 0D013) 5 9.52 (s, 1H), 8.33 (s, 1H), 7.29 (d, 2H), 7.17 (d, 2H), 3.52 (s, 3H), 2.39 (s, 3H).
Step 5: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-344-methyl-24N-methy1-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]prop-2-enylidene]amino]thiourea A mixture of (E)-2-methy1-344-methy1-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.12 g) in Ethanol (10 mL) was heated at 80 C for 2 h. The mixture was cooled to ambient temperature and the precipitated solids were collected by filtration, washed with cold Ethanol and dried under vacuum to afford the title compound 0.2 g (65 %) as a yellow solid. LC/MS: Rt : 2.411min; MS: m/z = 541.7 (M)-; 1H NMR
(DMSO-d6): 5 11.71 (s, 1H), 9.67 (s, 1H), 8.32 (s, 1H), 7.98 (s, 1H), 7.56 -7.46 (m, 2H), 7.43 -7.30 (m, 3H), 7.30 -7.14 (m, 3H), 6.74 (s, 1H), 3.51 (s, 3H), 3.08 (p, J = 6.9 Hz, 2H), 2.34 (s, 3H), 2.06 - 1.98 (m, 3H), 1.18 (d, J = 6.9 Hz, 6H).
Example 17: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-344-methyl-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-17) A mixture of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-344-methyl-24N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.1g), Sodium acetate (0.091 g), Methyl bromoacetate (0.075 mL) was taken up in Ethanol (20 mL) and the mixture stirred at 40 C for 12 h. The mixture was diluted with water (50 mL) at ambient temperature and extracted with Ethyl acetate (2 X 50 mL). The combined organic layers were dried over anhydrous Sodium suphate and evaporated invacuo and the residue obtained was subjected to Silica gel Flash column chromatography using a gradient of Ethylacetate/Heptane to afford the title compound (0.08 g, 75 %) as a yellow solid. LC/MS: Rt: 2.498 min; MS: m/z = 583.4 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 5 8.33 (s, 1H), 8.10 (s, 1H), 7.55 - 7.46 (m, 4H), 7.41 (dd, J = 19.5, 8.0 Hz, 3H), 7.36 - 7.19 (m, 2H), 6.91 (s, 1H), 4.28 - 4.03 (m, 2H), 3.50(s, 3H), 2.28 (s, 3H), 1.98(d, J =
1.2 Hz, 3H), 1.19 -1.08 (m, 6H).
Example 18: Synthesis of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylideneamino]thiourea (0-18) Step 1: 24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-ol A mixture of 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (1.8 g) and Triisopropylborate (1.82 mL) was taken up in Tetrahydrofuran (30 mL) and cooled to -78 C. A
solution of n-BuLi (1.6 M in n-hexane, 4.827mL) was added and the mixture allowed to warm upto -20 C for 20 min. Acetic acid (1.5 mL) followed by Methanol (8 mL) was added and the mixture evaporated under reduced pressure. To the resultant residue, Methanol (2 mL), Water (12 mL) and a solution of Hydrogen Peroxide (20 % in water, 1.5 mL, 10.34 mmol) was added and the mixture stirred at ambient temperature for 12 h. The mixture was subsequently diluted with water (50 mL) and extracted with Ethyl acetate ( 2 X 50 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated invacuo and the resultant solid was purified by Silica gel flash column chromatography with a gradient of Ethyl acetate/Heptane as eluent to afford the desired product (1 g, 68%yield) as a white solid. LC/MS: Rt: 1.788 min; MS:
m/z = 286.3 (M+1)+;
1H NMR (300 MHz, DMSO-d6) 5 9.47 (s, 1H), 8.05 (s, 2H), 7.48 -7.37 (m, 2H), 7.32 (d, J = 8.6 Hz, 2H), 3.43 (s, 3H).
Step 2: 5-(2,2-diethoxyethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a solution of 24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-ol (0.25 g) in N,N-Dimethylacetamide (2 mL), was added KOH (0.098 g) followed by Bromoacetaldehyde diethylacetal (0.2 mL). The mixture was heated to 100 C for 2 h and subsequently cooled to room temperature. The mixture was diluted with water (20 mL) and extracted with Ethyl acetate Et0Ac (2 X 20 mL). The combined organic extracts were washed with a saturated solution of Sodium chloride, dried over anhydrous Sodium sulphate and evaporated under reduced pressure to afford the title ocmpoun as a pale yellow oil (0.25g, 71 %) . LC/MS: Rt : 2.23 min;
MS: m/z = 402.9 (M+1)+; 1H NMR (300 MHz, 0D0I3) 58.10 (s, 1H), 7.32 ¨ 7.21 (m, 1H), 7.16 (d, J
= 8.5 Hz, 3H), 4.72 (t, J = 5.1 Hz, 1H), 3.91 (d, J = 5.1 Hz, 1H), 3.77 ¨3.63 (m, 2H), 3.63 ¨3.48 (m, 3H), 3.46 (s, 2H), 3.30 (d, J = 5.5 Hz, 1H), 1.17 (td, J = 7.1, 1.8 Hz, 6H).
Step 3: 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyacetaldehyde To a solution of 5-(2,2-diethoxyethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.2 g) in Acetone (4 mL) was added a solution of Hydrochloric acid (1 N, 1 ml) and the mixture heated at 70 C for 5 h. The reaction was diluted with water (4 mL) and extracted with Ethyl acetate (2 X 10 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the resultant residue was subjected to flash column chromatography using a gradient of Ethyl acetate/Heptane to afford the title compound as a colorless oil (0.14 g, 86%). LC/MS: Rt : 1.612 min; MS: m/z = 327 (M+1)+; 1H
NMR (300 MHz, 0D0I3) 59.85 (s, 1H), 8.17 (s, 2H), 7.36 (d, J = 9.0 Hz, 2H), 7.25 (d, J = 8.4 Hz, 2H), 4.61 (s, 2H), 3.54 (s,3H).
Step 4: 1-(2-isopropylpheny1)-3-[(E)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylideneamino]thiourea A mixture of 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyacetaldehyde (0.15 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.10 g) in Ethanol ( 5 mL) was heated at 80 C for 1 h.
Subsequently, the mixture was evaporated under reduced pressure to get the title compound as a white solid (0.16 g, 67 %). LC/MS: Rt : 2.187 min; MS: m/z = 519.65 (M+1)+; 1H
NMR (300 MHz, DMSO-d6) 6 11.73 (s, 1H), 9.82 (s, 1H), 8.34 (s, 2H), 7.57 (t, J = 5.2 Hz, 1H), 7.51 ¨ 7.39 (m, 2H), 7.36 (s, 2H), 7.30 (dd, J = 11.3, 5.3 Hz, 2H), 7.27 ¨ 7.11 (m, 3H), 4.77 (d, J
= 5.2 Hz, 2H), 3.45 (s, 3H), 3.02 (p, J = 6.9 Hz, 2H), 1.12 (d, J = 6.9 Hz, 6H).
Example 19: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylidenehydrazono]thiazolidin-4-one (0-19) A mixture of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylideneamino]thiourea (0.1 g), Sodium acetate (0.095 g), Methyl bromoacetate (0.078 mL) in Ethanol (20 mL) was stirred at 40 C for 12 h. The mixture was subsequently diluted with Water (50 mL) and extracted with Ethyl acetate (2 X 20 mL). The combined extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was purified by Silica gel flash column chromatography using a gradient of Ethyl acetate and heptane as eluent to afford the title compound (0.06 g, 56 %) as a white solid. LC/MS: Rt: 2.25 min; MS: m/z = 559.3 (M+1)+. 1H NMR (300 MHz, DMSO-d6) 6 8.256 (s, 2H), 7.672 (m, 1H), 7.431-7.462 (m, 4H), 7.327 ¨7.356 (m, 3H), 7.195 ¨ 7.251 (m, 1H), 4.79 (d, J= 4.5Hz, 2H), 4.112 (m, 2H), 3.443 (s, 3H), 2.702-2.790(m, 1H), 1.096 ¨ 1.127 (m, 6H).
Example 20: Synthesis of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropylideneamino]thiourea (0-20) Step 1: 5-(2,2-dimethoxy-1-methyl-ethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine A mixture of 24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-ol (0.4 g), Potassium hydroxide (0.158 g) and 2-bromo-1,1-dimethoxy-propane (0.4 mL)in N,N-Dimethylacetamide (4 mL)was heated at 100 C for 24 h.The mixture was cooled to ambient temperature and water (50 mL) was added and the mixture extracted with Ethyl acetate ( 2 X 30 mL). The combined organic layer was washed with a saturated solution of Sodium chloride and dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the crude obtained was purified by Silica gel flash column chromatography using a gradient of Ethyl acetate/Hepatane to obtain the title compound (0.1 g, 18 %). LC/MS: Rt: 2.144 min; MS: m/z = 388.4 (M+1)+; 1H NMR (300 MHz, Chloroform-d) 8.14 (s, 2H), 7.36 (s, 3H), 7.25 (s, 2H), 7.16 (s, 1H), 3.51 (s, 2H), 3.43 (d, J = 5.7 Hz, 4H), 3.39 (t, J
= 2.8 Hz, 5H).
Step 2: 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropanal A solution of 5-(2,2-dimethoxy-1-methyl-ethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.1 g) and a solution of Hydrochloric acid (IN, 1 mL) was taken up in in Acetone (4 mL) and heated at 70 C for 12 h. The reaction was diluted with water (20 mL) and extracted with Ethyl acetate ( 2 X 20 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated under reduced pressure to get the title compound. (0.07 g, 79.4 %) LC/MS: Rt: 1.685 min; MS: m/z = 342.2 (M+1)+; 1H NMR (300 MHz, 0D0I3) 6 9.67 (s, 1H), 8.08 (s, 2H), 7.26 (dd, J =
7.5, 5.1 Hz, 2H), 7.16 (d, J = 7.9 Hz, 2H), 4.417-4.444 (m, 1H),3.43 (s, 3H), 1.59 (d, J = 7.5 Hz, 3H).
Step 3: 1-(2-isopropylpheny1)-3-[(E)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropylideneamino]thiourea The mixture of 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropanal (0.15 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.09 g) in Ethanol (2 mL) was heated at 80 C for 1 h. The mixture was evaporated under reduced pressure and the residue subjected to Silica gel column chromatography to get the title compound (0.16 g, 68 %). LC/MS: Rt : 2.275 min; MS: m/z = 533.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.63 (s, 1H), 9.81 (s, 1H), 8.34 (s, 2H), 7.51 -7.40 (m, 2H), 7.38 (d, J = 6.3 Hz, 1H), 7.35 - 7.22 (m, 4H), 7.22 -7.11 (m, 2H), 4.97 (p, J = 6.4 Hz, 2H), 3.44 (s, 3H), 3.01 (p, J = 6.9 Hz, 2H), 1.49 (d, J = 6.3 Hz, 3H), 1.11 (dd, J
= 6.9, 2.4 Hz, 7H).
Example 21: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2424N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]oxypropylidenehydrazono]thiazolidin-4-one (C-21) A mixture of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropylideneamino]thiourea (0.1 g), Sodium acetate (0.092 g) and Methyl bromoacetate (0.076mL) in Ethanol (20 mL) was heated at 40 C for 12 h. The mixture was cooled to ambient temperature diluted with Water (50 mL) and extracted with Ethyl acetate ( 2 X
15 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate and the were evaporated invacuo and the resultant residue was subjected to flash column chromatography with Silica gel, eluting with a Ethyl acetate/Heptane gradient wo get the title compound as a yellow solid 0.108 g (70 %). LC/MS: Rt: 2.309 min; MS: m/z = 573.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 8.23 (d, J = 2.0 Hz, 2H), 7.57 (t, J = 5.4 Hz, 1H), 7.52 -7.39 (m, 4H), 7.39 -7.28 (m, 3H), 7.20 (d, J
= 7.9 Hz, 1H), 5.03 (q, J = 6.1 Hz, 1H), 4.40 - 3.93 (m, 2H), 3.44 (s, 3H), 1.42 (dd, J = 6.4, 1.7 Hz, 3H), 1.16 - 1.02 (m, 6H).
Example 22: Synthesis of 1-(2-isopropylpheny1)-3-[(E)42-methyl-344-methyl-24N-methy1-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]propylidene]amino]thiourea (0-22) Step 1: To the solution of (E)-2-methyl-344-methyl-2-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) in Ethyl acetate (5 mL) was added 10 %
Palladium on charcoal (0.02 g) and the mixture stirred under a Hydrogen atmosphere via a gas bladder for 12 h. The mixture was filtered through a Celite bed and evaporated under reduced pressure, the residue obtained subjected to flash column chromatography to afford the desired product (0.11 g). LC/MS Rt: 2.166 min; MS: m/z = 354.4 (M+1)+.
Step 2: 1-(2-isopropylpheny1)-3-REH2-methyl-3-[4-methyl-2-[N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]propylidene]amino]thiourea A mixture of 2-methyl-3-[4-methyl-2-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]propanal (0.1 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.06 g) in Ethanol (2 mL) was heated at 80 C
for 2 h. The rmixture was evaporated invacuo and the residue obtained was subjected to flash column chromatography to afford the desired product (0.13 g, 84 %) as a yellow solid. LC/MS Rt:
2.374min; MS: m/z = 545.6 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.42 (s, 1H), 9.49 (s, 1H), 8.13(s, 1H), 7.48 - 7.42 (m, 3H), 7.38 - 7.14 (m, 6H), 3.46(s, 3H), 2.91 (ddd, J =47.9, 13.5, 7.0 Hz, 2H), 2.33 (s, 3H).
Example 23: Synthesis of N-methyl-5-RE,3E)-2-methyl-3-[(3R,4R,5S,65)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxyimino-prop-1-eny1FN-[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (C-23) (E)-2-methyl-3-[24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.17 g), 0-[(3R,4R,55,65)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]hydroxylamine (0.123 g) and Concentrated hydrochloric acid solution (1.5 mL) was taken in Ethanol (15 mL) and the mixture heated to 80 C for 48 h. The mixture was diluted with Ethyl acetate (20 mL) and the organic layer separated, dried over anhydrous Sodium sulphate, evaporated invacuo and the residue subjected to flash column chromatography on Silica gel eluting with a gradient of Ethyl acetate and n-heptane to afford the title compound (0.055 g, 18 %). LC/MS: Rt: 2.278 min; MS: m/z =
541 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 6 8.51 (s, 1H), 8.09 (s, OH), 7.68 - 7.21 (m, 2H), 6.71 (s, 1H), 5.37 (dd, J =
27.0, 2.0 Hz, 1H), 3.52 (s, 2H), 3.44 -3.36 (m, 6H), 2.03 (d, J = 1.2 Hz, 2H), 1.83 (d, J = 1.4 Hz, 1H), 1.16 (d, J = 5.9 Hz, 2H).
Example 24: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-[2-methyl-3-[4-methyl-2-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]propylidene]hydrazono]thiazolidin-4-one (0-24) A mixture of 1-(2-isopropylpheny1)-3-[(E)42-methyl-314-methyl-2-[N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]propylidene]amino]thiourea (0.07 g), Sodium acetate (0.063 g), Methyl bromoacetate (0.04 mL) in Ethanol (10 mL) was stirred at 40 C for 12 h. The reaction mixture was cooled to ambient temperature, diluted with Water (50 mL), Sodium hydroxide solution (1 N, 2 mL) and extracted with Ethyl acetate (2 X 50 mL). The combined organic extracts were dried over anhydrous Sodium sulphate, evaporated invacuo and the residue subjected to flash column chromatography on Silic gel, eluting with a gradient of Ethyl acetate and Heptane to obtain the title compound as a white solid 0.05 g (67 %). LC/MS: Rt: 2.409 min; MS: m/z = 585.4 (M+1)+. 1H NMR
(300 MHz, DMSO-d6) 6 8.05 (d, J = 8.2 Hz, 1H), 7.54 (dd, J = 7.6, 5.3 Hz, 1H), 7.46 (dt, J = 7.7, 3.0 Hz, 4H), 7.40 -7.23 (m, 3H), 7.27 -7.11 (m, 1H), 4.28 - 3.86 (m, 2H), 3.45 (s, 3H), 2.77 -2.61 (m, 1H), 2.27(d, J =2.5 Hz, 3H), 1.16 - 0.92 (m, 10H).
Example 25: Synthesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-3424N-methyl-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]amino]imidazolidine-2,4-dione (0-25) (E)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.227 g) and 3-amino-1-(2-isopropylphenyl)imidazolidine-2,4-dione (0.157 g) were taken up in Ethanol (10 mL. 2 drops of conc. Hydrochloric acid solution was added and the mixture heated to 80 C for 3 h. The mixture was evaporated invacuo and the residue taken up in Ethyl acetate and washed with a saturated solution of Sodium bicarbonate solution. The organic layer was separated, dried and evaporated to obtain a residue which was subjected to preparative HPLC to get the title compound (0.058 g, 13 %), LC/MS: Rt: 2.26 min; MS: m/z = 553.8 (M).
Example 26: Synthesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-3464N-methyl-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enylidene]amino]thiourea (0-26) Step 1: Synthesis of 6-chloro-N[4-(trifluoromethoxy)phenyl]pyridazin-3-amine A mixture of 3,6 Dichloro pyridazine (0.2 g) and 4-(trifluoromethoxy) aniline (0.180 g) was taken up in in Acetic acid (3 mL) and heated at 90 C for 4 h. The mixture was cooled to ambient temperature, neutralized with Sodium bicarbonate solution and extracted with Ethyl acetate. The organic layer was dried over anhydrous Sodium sulfate and concentrated under reduced pressure and the residue obtained, was purified by column chromatography using Ethyl acetate and heptane as eluent to offer the desired compound as off-white solid (0.150 g, 51 %).
LC/MS: Rt : 1.841 min;
MS: m /z = 290.25 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 9.69 (s, 1H), 7.89 ¨
7.74 (m, 2H), 7.62 (d, J = 9.3 Hz, 1H), 7.35 (d, J = 8.6 Hz, 2H), 7.22 (d, J = 9.3 Hz, 1H).
Step 2: Sythesis of 6-chloro-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine To a stirred solution of 6-chloro-N[4-(trifluoromethoxy)phenyl]pyridazin-3-amine (2.6 g) in dry DMF (35 mL) was added Sodium hydride (0.323 g) at 0 C and stirred for 10 min.
Methyl iodide (2.55 g) was added and the mixture stirred at ambient temperature for 12 h.
Saturated ammoniun chloride solution was added and the mixture extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure and the residue obtained was subjected to flash column chromatography to get the title compound as a light brown solid. (1.9 g, 70%). LC/MS: Rt : 1.996 min; MS: m/z = 304.1 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 7.55 ¨ 7.41 (m, 5H), 6.98 (d, J = 9.5 Hz, 1H), 3.47 (s, 3H).
Step 3: Sythesis of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enal A mixture of 6-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (1.8 g), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.434 g), Cesium carbonate (3.9 g), and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3 g) was taken up in a mixture of Dioxan (4 mL) and water (16 mL) and degassed with Nitrogen gas for 10 min and subsequently heated at 95 C for 2 h. The mixture was diluted with 1N HCI
solution, neutralized with Sodium bicarbonate solution and filtered through Celite. The filtrate was extracted with Ethyl acetate and the extracts dried over anhydrous Sodium sulfate and evaporated invacuo to obtain a residue which was subjected to Silica gel flash column chromatography to obtain the desired compound as an off-white solid (1 g, 57 %). LC/MS: Rt : 2.00 min; MS: m/z =
338.5 (M+1)+; 1H
NMR (300 MHz, DMSO-d6) 5 9.63 (s, 1H), 7.63 (d, J = 9.5 Hz, 1H), 7.65 - 7.23 (m, 5H), 6.97 (d, J
= 9.5 Hz, 1H), 3.57 (s, 3H), 2.13 (d, J = 1.2 Hz, 3H).
Step 4: Sythesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]pyridazin-3-yl]prop-2-enylidene]amino]thiourea A mixture of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enal (0.25 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.150 g) in Methanol (4 mL) was heated at 80 C for 3 h. The mixture was evaporated, Water and Ethyl acetate added and the ethyl acetate layer separated, dried evaporated invacuo to obtain a residue which was subjected to flash column chromatography to obtain the title compound as a brown solid (0.190 g, 47 %).
LC/MS: Rt : 2.256 min; MS: m/z = 529.3 (M+1,)+; 1H NMR (300 MHz, DMSO-d6) 5 11.77 (s, 1H), 9.74 (s, 1H), 7.99 (s, 1H), 7.79 - 7.44 (m, 5H), 7.37 - 7.12 (m, 2H), 6.94 (d, J = 9.5 Hz, 1H), 6.79 (s, 1H), 3.54 (s, 3H), 3.19 - 3.02 (m, 1H), 2.44 - 2.23 (m, 3H), 1.19 (d, J = 6.9 Hz, 6H).
Example 27: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-346-[N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-27) A mixture of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]pyridazin-3-yl]prop-2-enylidene]amino]thiourea (0.158 g), Sodium acetate (0.049 g), and Methylbromo acetate (0.137 g) in Methanol (4 mL) was stirred for 12 h. The mixture was evaporated invacuo and the residuce was subjected to Silica gel column chromatography eluting with a gradient of Dichloromethane and methanol to obtain the title compound as a brown solid (0.09 g, 50 %). LC/MS: Rt : 2.261 min; MS: m/z = 569.90 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 8.08 (s, 1H), 7.55 -7.38 (m, 7H), 7.38 - 7.20 (m, 2H), 6.97 - 6.87 (m, 2H), 4.29 -4.04 (m, 2H), 3.54 (s, 3H), 2.90 - 2.67 (m, 1H), 2.30 (d, J = 1.2 Hz, 3H), 1.14 (t, J = 6.7 Hz, 6H).
Example 28: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxypropylidenehydrazono]thiazolidin-4-one (0-28) Step 1: Synthesis of N-methyl-6-(1-methylallyloxy)-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine To a stirred solution of 6-chloro-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (1 g) and ally! alcohol (0.475 g) in N, N-Dimethylformamide (15 mL) at 0 C was added Sodium hydride (0.160 g) and the mixture stirred at ambient temperature for 12 h. Saturated Ammonium chloride .. solution was subsequently added and the mixture extracted with Ethy acetate. The Ethyl acetate extracts were separated, dried over anhydrous Sodium sulphate and evaporated invacuo, and the residue obtained was subjected to flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to get the desired product as a brown solid (0.56 g, 50 %). LC/MS: Rt : 2.193 min; MS: m/z = 340.5 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 7.38 (s, 4H), 7.06 (d, J = 9.6 Hz, 1H), 6.96 (d, J = 9.6 Hz, 1H), 6.00 (ddd, J = 17.3, 10.6, 5.5 Hz, 1H), 5.69 (dtd, J = 7.8, 6.4, 5.1 Hz, 1H), 5.29 (dt, J = 17.3, 1.5 Hz, 1H), 5.15 (dt, J = 10.6, 1.4 Hz, 1H), 3.42 (s, 3H), 1.40 (d, J = 6.5 Hz, 3H).
Step 2: 2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxypropanal A mixture of N-methyl-6-(1-methylallyloxy)-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (0.580 g), Osmium tetroxide (0.022 g) in Water (2 mL) and Sodium periodate (1 g) was taken up in a mixture of 1,4 Dioxane (16 mL) and water (2 mL) and the mixture stirred at ambient temperature for 4 h. 2 % Sodium sulfite solution was added and the mixture extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure to get a solid residue which was purified by Silica gel flash column chromatography using Ethyl acetate/heptane mixture as eluent to afford the title compound. (0.32 g, 55 %). LC/MS: Rt:
1.420 min; MS: m/z = 342.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 59.65 (d, J = 1.3 Hz, 1H), 7.39 (d, J = 6.7 Hz, 5H), 7.11 (d, J = 1.7 Hz, 1H), 3.42 (s, 3H), 3.28 (d, J = 2.8 Hz, 1H), 1.44 (d, J = 7.1 Hz, 3H).
Step 3:1-(2-isopropylpheny1)-3-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxypropylideneamino]thiourea A mixture of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal (0.220 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.150 g) was taken up in Tetrahydrofuran (5 mL) and heated at 50 C for 4 h. The mixture was diluted with Water and extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was subjected to Silica gel flash column chromatography to obtain the title compound as a viscous liquid. (0.130 g, 38 %). LC/MS: Rt : 2.233 min; MS: m/z = 533.3 (M+1)+; 1H
NMR (300 MHz, DMSO-d6) 5 11.62 (s, 1H), 9.62 (s, 1H), 7.66 (d, J = 4.4 Hz, 1H), 7.47 - 6.86 (m, 11H), 5.76 (dd, J = 6.6, 4.5 Hz, 1H), 3.43 (s, 3H), 3.07 - 2.93 (m, 1H), 1.56 (d, J = 6.5 Hz, 3H), 1.15 (d, J = 6.9 Hz, 7H).
Step 4: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]
pyridazin-3-yl]oxypropylidenehydrazono]thiazolidin-4-one A mixture of 1-(2-isopropylpheny1)-3-RE)-2464N-methyl-4-(trifluoromethoxy)anilino]Pyridazine -3-yl]oxypropylideneamino]thiourea (0.160 g), Sodium acetate (0.050 g), and Methyl bromo acetate (0.138 g) in Methanol (4 mL) was stirred at ambient temperature for 12 h. The reaction mixture was subsequently diluted with Water and extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphte and evaporated invacuo and the residue subjected to Silica gel flash column chromatography to afford the title compound (0.06 g, 37 %).
LC/MS: Rt : 2.264 min;
MS: m /z = 573.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 57.55 (dd, J = 12.8, 4.1 Hz, 1H), 7.47 -7.13 (m, 9H), 7.08 (dd, J = 7.8, 1.4 Hz, 1H), 7.02 - 6.77 (m, 2H), 5.62 (ddd, J = 6.4, 4.3, 2.0 Hz, 1H), 4.36 - 3.82 (m, 2H), 3.29 (s, 3H), 2.72 -2.55 (m, 1H), 1.36 (d, J = 6.6 Hz, 3H), 0.99 (dd, J =
6.9, 1.9 Hz, 8H).
Example 29: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy) anilino]pyridazin-3-yl]oxyethylidenehydrazono]thiazolidin-4-one (0-29) Step 1: Synthesis of 6-allyloxy-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine To a stirred solution of Ally! alcohol (1 g) in N, N-Dimethylformamide (15 mL) at 0 C was added Sodium hydride (0.320 g) and the mixture stirred for 20 min. A solution of 6-chloro-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (2.7 g) in N,N-Dimethylformamide (5 mL) was added drop-wise and the mixture stirred for a further 3 h. Saturated Ammoniun chloride solution was subsequently added, the mixture extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated invacuo. The residue obtained was subjected to Silica gel flash column chromatography to obtain the title compound as a white solid (2.5 g, 86 %).
LC/MS: Rt : 2.086 min; MS: m/z = 326.25 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 57.38 (d, J = 1.5 Hz, 4H), 7.13 ¨ 6.96 (m, 2H), 6.10 (ddt, J = 17.3, 10.7, 5.5 Hz, 1H), 5.40 (dq, J = 17.3, 1.7 Hz, 1H), 5.26 (dq, J = 10.5, 1.5 Hz, 1H), 4.87 (dt, J = 5.5, 1.5 Hz, 2H), 3.43 (s, 3H).
Step 2: 2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyacetaldehyde A mixture of 6-allyloxy-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (0.22 g), Sodium periodate (0.434 g) and Osmium tetraoxide (catalytic) was taken up in 1,4 -Dioxane (6 mL) and Water (1 mL) and the mixture stirred at ambient temperature for 12 h. The mixture was subsequently quenched with Sodium sulfite solution and extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and n-Heptane to afford the desired compound as an off-white solid. (0.150 g, 68 %).
LC/MS: Rt : 1.382 min; MS: m/z = 328.15 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 7.45 ¨ 7.31 (m, 4H), 7.03 (q, J = 9.6 Hz, 2H), 6.40 (d, J = 7.8 Hz, 1H), 4.82 (dt, J = 7.8, 5.1 Hz, 1H), 4.21 (h, J = 5.7 Hz, 2H), 3.43 (s, 3H), 3.34 (s, 4H), 1.39 ¨ 1.25 (m, 1H), 1.24 (s, 3H).
Step 3: Synthesis of 1-(2-isopropylpheny1)-3-RE)-2464N-methyl-4-(trifluoromethoxy) anilino]
pyridazin-3-yl]oxyethylideneamino]thiourea A mixture of 2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyacetaldehyde (0.530 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.338 g) in Tetrahydrofuran (5 mL) was heated at 50 C for 3 h. The mixture was diluted with Water and extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated under reduced pressure. The residue obtained was subjected to Silica gel flash column chromatography using a gradient of Ethyl acetate and Heptane to obtain the title compound as a white solid (0.2 g, 24 %). LC/MS: Rt : 2.175 min; MS: m / z = 519.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.71 (s, 1H), 9.73 (s, 1H), 7.72 (t, J = 5.0 Hz, 1H), 7.39 (s, 4H), 7.37 ¨ 7.21 (m, 3H), 7.18 (dd, J = 3.7, 2.3 Hz, 2H), 7.14 ¨ 7.03 (m, 2H), 5.04 (d, J = 4.9 Hz, 2H), 3.44 (s, 3H), 3.04 (p, J = 6.9 Hz, 1H), 1.15 (d, J = 6.8 Hz, 6H).
Step 4: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyethylidenehydrazono]thiazolidin-4-one A mixture of 1-(2-isopropylpheny1)-3-RE)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyethylideneamino]thiourea (0.090 g), Sodium acetate (0.029 g) and Methyl bromoacetate (0.080 g) in Tetrahydrofuran (2 mL) was stirred at ambient temperature for 12 h. The mixture was subsequently diluted with Water, extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated invacuo. The resultant solid was subjected to Silica gel flash column chromatography using Ethyl acetate/Heptane gradient to obtain the title compound as a white solid (0.070 g, 57 %). LC/MS Rt : 2.189 min; MS: m/z = 559.55 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 1H NMR (300 MHz, DMSO-d6) 6 7.47 (td, J = 7.9, 1.7 Hz, 3H), 7.43 ¨ 7.24 (m, 7H), 7.21 (d, J = 7.5 Hz, 1H), 7.05 (q, J = 9.3 Hz, 3H), 5.05 (d, J = 4.4 Hz, 2H), 4.31 ¨4.02 (m, 3H), 3.41 (d, J = 5.3 Hz, 12H), 2.75 (h, J = 6.8 Hz, 2H), 1.27 ¨ 1.07 (m, 9H).
Example 30: Synthesis of 1-[(E)-24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]ethylideneamino]-3-(2-isopropylphenyl)thiourea (0-30) Step 1: 5-Brom-4,6-dimethyl-pyridin-2-amine A mixture of 4,6-dimethylpyridin-2-amine (3 g) and Bromine ( 1.39 mL) taken up in Acetonitrile (30 mL) was stirred at ambient temperature for 1 h. The mixture was diluted with Water (100 mL) and the precipitate was collected by filteration and dried to afford the title product as a off white solid (3.8 g, 77%). LC/MS: Rt: 1.2 min; MS: m/z = 203 (M+1)+; 1H NMR (300 MHz, Chloroform-d) 57.28 (s, 1H), 6.37 (s, 2H), 2.43 - 2.12 (m, 6H).
Step 2: 5-bromo-4,6-dimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine A mixture of 5-Bromo-4,6-dimethyl-pyridin-2-amine (2 g), Cesium carbonate (6.46 g), 4-Trifluoromethoxy iodobenzene (4.29 g), Palladium (II) acetate (0.22 g, 0.99 mmol) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.57 g) was taken up in Toleune (40 mL) and degassed with nitrogen gas and heated at 120 C for 5 h. The reaction was diluted with Water (50 mL) and extracted with Ethyl acetate (2 X 30 mL) and the combined organic extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure. The residue was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to obtain the title compound as an off white solid (2.7 g, 75 %).
LC/MS: Rt: 2.44 min; MS:
m/z = 363.2 (M+2)+; 1H NMR (300 MHz, CDCI3) 6 7.36 (d, J = 9.0 Hz, 2H), 7.24 (d, J = 8.8 Hz, 2H), 2.66 (s, 3H), 2.39 (s, 3H).
Step 3: 5-bromo-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine To the solution of 5-bromo-4,6-dimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine (2.5 g) in N, N-Dimethylformamide (30 mL) at 0 C was added Sodium hydride (60 %
dispersion in mineral oil, 0.415 g) portion wise. Methyl iodide (0.7 mL) was added and the mixture stirred at 0 C for 1 h.
The mixture was poured into ice water and extracted with Ethyl acetate (2 X 30 mL) and the extracts dried over anhydrous Sodium sulphate. The extracts were evaporated invacuo and the residue subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the title compound as an off white solid (2.5 g, 96 %).
LC/MS: Rt: 2.628 min;
MS: m/z = 375.2 (M+2)+; 1H NMR (300 MHz, CDCI3) 57.18 (d, J = 5.3 Hz, 5H), 6.20 (s, 1H), 3.41 (s, 3H), 2.55 (d, J = 2.6 Hz, 3H), 2.16 (s, 3H).
.. Step 4: 2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]pyridin-3-ol A mixture of 5-bromo-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine (0.5 g), Tris(dibenzylideneacetone)dipalladium(0) (0.12 g), 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.057 g) and Potassium hydroxide (0.15 g) was taken up in 1,4-Dioxan (4 mL) and Water (4 mL) and heated at 90 C for 2 h. The mixture was cooled to ambient temperature and .. diluted with Water (50 mL) and extracted with Ethyl acetate (2 X 30 mL).The combined organic layer was dried over anhydrous Sodium sulphate evaporated invacuo and the residue was subjected to Silica gel flash column chromatography to get the title compound as an off white solid (0.4 g, 96%). LC/MS: Rt: 1.614 min; MS: m/z = 313.25 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 8.25 (s, 1H), 7.22 (s, 1H), 7.10 (d, J = 9.1 Hz, 1H), 6.59 (s, 1H), 3.28 (s, 3H), 2.29 (s, 3H), 2.11 (s, .. 3H).
Step 5: 5-(2, 2-diethoxyethoxy)-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine A mixture of 2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]pyridin-3-ol (0.3 g), Potassium hydroxide (0.27 g) and Bromoacetaldehyde diethylacetal (0.217 mL) was taken up in N,N-Dimethylacetamide (4 mL) and heated at 100 C for 1 h. The mixture was subsequently cooled to ambient temperature and Water (50 mL) was added and extracted with Ethyl acetate (2 X 20 mL).
The combined Ethyl acetate extracts were washed with brine, dried over anhydrous Sodium sulphate and evaporated invacuo to get the title compound as a pale yellow oil (0.27 g, 66 %).
LC/MS: Rt : 2.45 min; MS: m/z = 429.3 (M); 1H NMR (DMSO-d6): 1H NMR (300 MHz, DMSO-d6) 57.32 (d, J = 2.0 Hz, 4H), 6.42 (s, 1H), 4.78 (t, J = 5.1 Hz, 1H), 3.79 ¨ 3.46 (m, 5H), 2.32 (s, 4H), 2.13 (s, 3H), 1.15 (t, J = 7.0 Hz, 6H).
Step 6: 24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]acetaldehyde To the solution of 5-(2,2-diethoxyethoxy)-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl] pyridin-2-amine (0.25 g) in Acetone (5 mL) was added a solution of Hydrochloric acid (1 mL). The mixture was heated at 70 C for 2 h. The mixture was subsequently basified with sat.
Sodium bicarbonate solution and extracted with Ethyl acetate (2 X 20 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated invacuo to get the title compound as a pale yellow oil (0.2 g, 96 %). LC/MS: Rt : 1.56 min; MS: m/z = 355 (M); 1H NMR
(DMSO-d6): 1H NMR
(300 MHz, DMSO-d6) 59.70 (s, OH), 7.32 (d, J = 5.0 Hz, 8H), 6.43 (d, J = 5.5 Hz, 1H), 5.18 (s, OH), 4.55 (s, 1H), 2.30 (d, J = 6.2 Hz, 3H), 2.17 ¨ 1.91 (m, 3H).
Step 7: 1-[(E)-24[2,4-dimethyl-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]ethylideneamino]-3-(2-isopropylphenyl)thiourea A mixture of 24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]acetaldehyde (0.15 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.09 g) in Ethanol (4 mL) was heated at 80 C
for 2 h. The mixture was evaporated under reduced pressure and the residue obtained was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to obtain the title compound as a white solid. (0.16 g, 69 %). LC/MS:
Rt : 2.37 min; MS:
m/z = 546.3(M); 1H NMR (DMSO-d6) 5 11.69(s, 1H), 9.75(s, 1H), 7.70 (t, J = 5.4 Hz, 1H), 7.39 ¨
7.07 (m, 7H), 6.44 (s, 1H), 4.48 (d, J = 5.4 Hz, 2H), 2.34 (s, 3H), 2.15 (s, 3H), 1.14 (d, J = 6.8 Hz, 6H).
Example 31: Synthesis of (2Z)-2-[(E)-24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]ethylidenehydrazono]-3-(2-isopropylphenyl)thiazolidin-4-one (0-31) A mixture of 1-[(E)-24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]
ethylideneamino]-3-(2-isopropylphenyl)thiourea (0.1 g), Sodium acetate (0.09 g) and Methyl bromoacetate (0.056 mL) in Ethanol (4 mL) was stirred at 40 C for 12 h. The mixture was cooled to ambient temperature and diluted with Water (50 mL) and a solution of Sodium hydroxide (1 N, 1 mL) and extracted with Ethyl acetate (2 X 50 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate, evaporated invacuo and the residue subjected to Silica gel flash column chromatography to get the title compound as a yellow solid (0.042 g, 39 %). LC/MS: Rt:
2.41 min; MS: m/z = 586.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 7.75 (s, 1H), 7.48 (s, 1H), 7.32 (s, 7H), 7.24(s, 1H), 6.42 (s, 2H), 4.67 ¨ 4.37 (m, 4H), 4.16 (d, J = 20.4 Hz, 3H), 2.28(s, 8H), 2.10 (s, 6H), 1.12 (dd, J = 6.9, 5.0 Hz, 12H).
Ii Ar)N'G (I) Table C:
No. Ar Q A G R R1 M/z Rt [min]
CH H
. NH N CH H H3C H N-NI CH3 N---µ 515 1.95 F+F
F . S
H , N-N CH3 501 1.89 11 0 NH N CH H H3C F+F S
F
. CH3 r/
. cH3..../
I. 0 NH N CH H NN CH3 555 1.99 F+F
F I S
S H /
lO N¨Nr C H3 541 1.95 F+F
F H3C j S
IC)"/
C-5 ik CH3 cH3 /.. j- 555 1.97 0 NCH3 N CH H N m/
F+F NI% ...".
F OK,s N /
el NCH3 N CH H N'( r\I CH3 529.3 2.37 F+F * S
F
C-7 . CH3 CH3 /.......?" 569.4 2.49 . 0 NCH3 N CH H
F+F N---f C H3 F
OKS
CH3 H3C H /,õP
F+F N(CH3)2 I. 0 NC H 3 C-CH H H N /
NIf -N CH3 571.4 2.498 * S
F
No. Ar Q A G R R1 M/z Rt [min]
0-9 ipo c H3 NCH3 CH H 611.9 2.576 F+F N(CH3)2 N
F NN/
OK) 0-10 ip CH3 N.....1 NCH3 N CH H N-f."-- ' 586.3 2.102 F+F O S N- 0 C-11 . CH3 0 NCH3 N CH H cH3 1 , ,N H 572.3 2.149 F+F
F 0\,,,sr 0 0-12 * C H3 F+F 568.4 2.465 N...._a NV
F
S
0 [ C H3 0-13 a H3c cH3 1-N H
H NH
N(.1( NCH3 N CH H 532.3 2.134 F+F * 0 F
C
0-14 H3cH3 0 CH H
F+F ii N N, ,j- 539 2.18 y N
C-15 a H3c C H3 H
NLNW
NCH3 CH CH H 528.75 2.396 -if C H3 F+F * S
F
C-16 cH3 F+F H
N..._,NLN4." 543.7 2.411 40 õs C H3 F
0-17 1p C H3 40 cH3 0 NCH3 N CH CH3 583.4 2.498 F+F N--INLN4"-F 0\,s C H3 No. Ar Q A G R R1 M/z Rt [min]
0-18 a H3c c H3 H H 'Ts 0 NCH3 N CH H is F+F NyN-N
519.65 2.187 F S
0-19 ip C H3 40 cH3 7-O NCH3 N CH H 559.3 2.25 F+F N--1N-N-----"/
F Od\S
0-20 0 H3c c H3 H H
0 NCH3 N CH H N N o 533.3 2.275 F+F S
0 y 'I\lc H3 F
40 cH3 wr 573.3 2.309 F+F N..,N./7-1".
F
OKS
0-22 a H3c CH3 H H
0 NCH3 N CH CH3 I.
r\j)(NNj.s 545.65 2.374 F+F S C H3 F
0-23 c H3 o-01-13 0,, 0-cH3 cH3 0 NCH3 N CH H , 541 2.3 F+F N
H3C 0 0' \
F
¨
0-24 1p cH3 0 cH3 NCH3 N CH CH3 585.4 2.409 F+F m N
F 0\._.j C-25 H3c 40 cH3 -F+F O Nre N, /.?-.µ 553.8 2.26 y 1\V
0-26 a H3c C H3 H H
WI NCH3 CH N H lei NyN`r\j 529.3 2.256 F+F
No. Ar Q A G R R1 M/z Rt [min]
40, cH3 0 NCH3 CH N H c H3 569.9 2.261 * cH3 40o NCH3 CH N H c H, 573.4 2.264 F+F 0 NrN,Nr0 cH3 40o NCH3 CH N H cH3 ¨r 559.55 2.189 F+F
NNO
F+F CH3 C-0 NCH3 CH CH3 o NNAN 546.3 2.37 H H
C-31 cH3 CH3 cH3 586.4 2.419 F+F CH3 N
Biological examples:
Example B1: Action on Yellow fever mosquito (Aedes aegypti) For evaluating control of yellow fever mosquito (Aedes aegyptt) the test unit consisted of 96-well-5 microtiter plates containing 200plof tap water per well and 5-15 freshly hatched A. aegyptilarvae.
The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5p1, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at 28 1 C, 80 5 % RH
for 2 days. Larval 10 mortality was then visually assessed.
In this test, compounds 0-1, 0-2, 0-3, 0-4, 0-5, 0-6, 0-7, 0-9, 0-12, 0-16, 0-17, 0-23, 0-27, and 0-31 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B2: Action on Orchid thrips (dichromothrIps corbettt) Dichromothrtps corbetti adults used for bioassay were obtained from a colony maintained 15 continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1:1 mixture of acetone:water (vol:vol), plus Kinetic HV at a rate of 0.01%
v/v.
Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28 C for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.
In this test, compounds C-1, 0-3, 0-5, 0-6, 0-7, 0-9, 0-12, 0-14, 0-15, 0-16, 0-17, 0-23, 0-26, 0-27, and at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B3: Action on Boll weevil (Anthonomus grandis) For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well-microtiter plates containing an insect diet and 5-10 A. grandis eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO.
Different concentrations of formulated compounds were sprayed onto the insect diet at 5 pi, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 25 + 1 C and about 75 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds C-1, 0-2, 0-3, 0-4, 0-5, 0-6, 0-7, 0-8, 0-9, 0-12, 0-14, C-15, C-16, C-17, 0-22, 0-23, 0-26, 0-27, and 0-31 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B4: Action on Silverleaf whitefly (Bemista argentifolit) (adults) The active compounds were formulated by a Tecan liquid handler in 100%
cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100%
cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10m1 glass vials. A nonionic surfactant (Kinetic ) was included in the solution at a volume of 0.01% (v/v).
The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.
Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced.
The insects were collected using an aspirator and a nontoxic Tygone tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25 C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.
In this test, compounds C-3, C-5, C-6, C-7, C-8, C-12, C-15, C-16, C-17, C-22, C-23, and C-26 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B5: Action on Tobacco budworm (Heliothis virescens) For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO.
Different concentrations of formulated compounds were sprayed onto the insect diet at 10 pi, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 28 + 1 C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds C-1, 0-2, 0-3, 0-4, 0-5, 0-6, 0-7, 0-8, 0-9, 0-10, 0-11, 0-12, C-13, C-14, 0-15, 0-16, 0-17, 0-22, 0-23, 0-24, 0-26, 0-27, 0-30, and 0-31 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B6: Action on Diamond back moth (Plutella xylostella) The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water: acetone. Surfactant (Kinetic HV) is added at a rate of 0.01%
(vol/vol).The test solution is prepared at the day of use.
Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0-100%.
In this test, compounds 0-1, 0-2, 0-3, 0-4, 0-5, 0-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, 0-15, 0-16, 0-17, 0-18, 0-19, 0-20, 0-21, 0-23, 0-24, 0-26, 0-27, 0-28, 0-29, 0-30, and C-31 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B7: Action on Southern armyworm (Spodoptera eridania), 2nd instar larvae The active compounds were formulated by a Tecan liquid handler in 100%
cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100 %
cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20m1 glass vials. A nonionic surfactant (Kinetic ) was included in the solution at a volume of 0.01% (v/v).
The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.
Lima bean plants (variety Sieve) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 11 armyworm larvae were placed into the bag and the bags zipped closed.
Test plants were maintained in a growth room at about 25 C and about 20-40%
relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
In this test, compounds C-1, 0-2, 0-3, 0-4, 0-5, 0-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-15, 0-16, 0-17, 0-18, 0-19, 0-23, 0-26, 0-27, and 0-31 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
71 H NH Ar3 R11-1 110 H NH AO R11-5 72 H NH Ar3 R11-2 111 H NH AO R11-6 73 H NH Ar3 R11-3 112 H NH Art R11-7 74 H NH Ar3 R11-4 113 H NH Art R11-8 75 H NH Ar3 R11-5 114 H NH AO R11-9 76 H NH Ar3 R11-6 115 H NH Art R11-10 77 H NH Ar3 R11-7 116 H NH Art R11-11 78 H NH Ar3 R11-8 117 H NH Art R11-12 79 H NH Ar3 R11-9 118 H NH Art R11-13 80 H NH Ar3 R11-10 119 H NH Art R11-14 81 H NH Ar3 R11-11 120 H NH Art R11-15 82 H NH Ar3 R11-12 121 H NH Art R11-16 83 H NH Ar3 R11-13 122 H NH Art R11-17 84 H NH Ar3 R11-14 123 H NH Art R11-18 85 H NH Ar3 R11-15 124 H NH Art R11-19 86 H NH Ar3 R11-16 125 H NH Art R11-20 87 H NH Ar3 R11-17 126 H NH Art R11-21 88 H NH Ar3 R11-18 127 H NH Art R11-22 89 H NH Ar3 R11-19 128 H NH Art R11-23 90 H NH Ar3 R11-20 129 H NH Art R11-24 91 H NH Ar3 R11-21 130 H NH Art R11-25 92 H NH Ar3 R11-22 131 H NH Art R11-26 93 H NH Ar3 R11-23 132 H NH Art R11-27 94 H NH Ar3 R11-24 133 H NH Art R11-28 95 H NH Ar3 R11-25 134 H NH Art R11-29 96 H NH Ar3 R11-26 135 H NH Art A11-la 97 H NH Ar3 R11-27 136 H NH AO A11-lb 98 H NH Ar3 R11-28 137 H NH Art A11-2a 99 H NH Ar3 R11-29 138 H NH Art A11-2b 100 H NH Ar3 A11-la 139 H NH AO A11-3a 101 H NH Ar3 A11-lb 140 H NH AO A11-3b 102 H NH Ar3 A11-2a 141 H NH Ar5 R11-1 103 H NH Ar3 A11-2b 142 H NH Ar5 R11-2 104 H NH Ar3 A11-3a 143 H NH Ar5 R11-3 105 H NH AO A11-3b 144 H NH Ar5 R11-4 106 H NH Art R11-1 145 H NH Ar5 R11-5 107 H NH Art R11-2 146 H NH Ar5 R11-6 108 H NH Art R11-3 147 H NH Ar5 R11-7 109 H NH Art R11-4 148 H NH Ar5 R11-8 Line R Q Ar D Line R Q Ar D
149 H NH Ar5 R11-9 188 H NH Ar6 R11-13 150 H NH Ar5 R11-10 189 H NH Ar6 R11-14 151 H NH Ar5 R11-11 190 H NH Ar6 R11-15 152 H NH Ar5 R11-12 191 H NH Ar6 R11-16 153 H NH Ar5 R11-13 192 H NH Ar6 R11-17 154 H NH Ar5 R11-14 193 H NH Ar6 R11-18 155 H NH Ar5 R11-15 194 H NH Ar6 R11-19 156 H NH Ar5 R11-16 195 H NH Ar6 R11-20 157 H NH Ar5 R11-17 196 H NH Ar6 R11-21 158 H NH Ar5 R11-18 197 H NH Ar6 R11-22 159 H NH Ar5 R11-19 198 H NH Ar6 R11-23 160 H NH Ar5 R11-20 199 H NH Ar6 R11-24 161 H NH Ar5 R11-21 200 H NH Ar6 R11-25 162 H NH Ar5 R11-22 201 H NH Ar6 R11-26 163 H NH Ar5 R11-23 202 H NH Ar6 R11-27 164 H NH Ar5 R11-24 203 H NH Ar6 R11-28 165 H NH Ar5 R11-25 204 H NH Ar6 R11-29 166 H NH Ar5 R11-26 205 H NH Ar6 A11-la 167 H NH Ar5 R11-27 206 H NH Ar6 A11-1b 168 H NH Ar5 R11-28 207 H NH Ar6 A11-2a 169 H NH Ar5 R11-29 208 H NH Ar6 A11-2b 170 H NH Ar5 A11-la 209 H NH Ar6 A11-3a 171 H NH Ar5 A11-lb 210 H NH Ar6 A11-3b 172 H NH Ar5 A11-2a 211 H NH Ar7 R11-1 173 H NH Ar5 A11-2b 212 H NH Ar7 R11-2 174 H NH Ar5 A11-3a 213 H NH Ar7 R11-3 175 H NH Ar5 A11-3b 214 H NH AC R11-4 176 H NH Ar6 R11-1 215 H NH Ar7 R11-5 177 H NH Ar6 R11-2 216 H NH Ar7 R11-6 178 H NH Ar6 R11-3 217 H NH AC R11-7 179 H NH Ar6 R11-4 218 H NH AC R11-8 180 H NH Ar6 R11-5 219 H NH AC R11-9 181 H NH Ar6 R11-6 220 H NH Ar7 R11-10 182 H NH Ar6 R11-7 221 H NH AC R11-11 183 H NH Ar6 R11-8 222 H NH AC R11-12 184 H NH Ar6 R11-9 223 H NH Ar7 R11-13 185 H NH Ar6 R11-10 224 H NH Ar7 R11-14 186 H NH Ar6 R11-11 225 H NH Ar7 R11-15 187 H NH Ar6 R11-12 226 H NH Ar7 R11-16 Line R Q Ar D Line R Q Ar D
227 H NH AC R11-17 266 H NH Ar8 R11-21 228 H NH AC R11-18 267 H NH Ar8 R11-22 229 H NH Ar7 R11-19 268 H NH Ar8 R11-23 230 H NH Ar7 R11-20 269 H NH Ar8 R11-24 231 H NH AC R11-21 270 H NH Ar8 R11-25 232 H NH Ar7 R11-22 271 H NH Ar8 R11-26 233 H NH Ar7 R11-23 272 H NH Ar8 R11-27 234 H NH Ar7 R11-24 273 H NH Ar8 R11-28 235 H NH Ar7 R11-25 274 H NH Ar8 R11-29 236 H NH Ar7 R11-26 275 H NH Ar8 A11-la 237 H NH Ar7 R11-27 276 H NH Ar8 A11-1b 238 H NH Ar7 R11-28 277 H NH Ar8 A11-2a 239 H NH Ar7 R11-29 278 H NH Ar8 A11-2b 240 H NH Ar7 A11-la 279 H NH Ar8 A11-3a 241 H NH Ar7 A11-lb 280 H NH Ar8 A11-3b 242 H NH Ar7 A11-2a 281 H NH Ar9 R11-1 243 H NH Ar7 A11-2b 282 H NH Ar9 R11-2 244 H NH Ar7 A11-3a 283 H NH Ar9 R11-3 245 H NH Ar7 A11-3b 284 H NH Ar9 R11-4 246 H NH Ar8 R11-1 285 H NH Ar9 R11-5 247 H NH Ar8 R11-2 286 H NH Ar9 R11-6 248 H NH Ar8 R11-3 287 H NH Ar9 R11-7 249 H NH Ar8 R11-4 288 H NH Ar9 R11-8 250 H NH Ar8 R11-5 289 H NH Ar9 R11-9 251 H NH Ar8 R11-6 290 H NH Ar9 R11-10 252 H NH Ar8 R11-7 291 H NH Ar9 R11-11 253 H NH Ar8 R11-8 292 H NH Ar9 R11-12 254 H NH Ar8 R11-9 293 H NH Ar9 R11-13 255 H NH Ar8 R11-10 294 H NH Ar9 R11-14 256 H NH Ar8 R11-11 295 H NH Ar9 R11-15 257 H NH Ar8 R11-12 296 H NH Ar9 R11-16 258 H NH Ar8 R11-13 297 H NH Ar9 R11-17 259 H NH Ar8 R11-14 298 H NH Ar9 R11-18 260 H NH Ar8 R11-15 299 H NH Ar9 R11-19 261 H NH Ar8 R11-16 300 H NH Ar9 R11-20 262 H NH Ar8 R11-17 301 H NH Ar9 R11-21 263 H NH Ar8 R11-18 302 H NH Ar9 R11-22 264 H NH Ar8 R11-19 303 H NH Ar9 R11-23 265 H NH Ar8 R11-20 304 H NH Ar9 R11-24 Line R Q Ar D Line R Q Ar D
305 H NH Ar9 R11-25 344 H NH Arl R11-29 306 H NH Ar9 R11-26 345 H NH Arl A11-la 307 H NH Ar9 R11-27 346 H NH Arlo A11-lb 308 H NH Ar9 R11-28 347 H NH Arlo A11-2a 309 H NH Ar9 R11-29 348 H NH Arl A11-2b 310 H NH Ar9 A11-la 349 H NH Arlo A11-3a 311 H NH Ar9 A11-lb 350 H NH Arlo A11-3b 312 H NH Ar9 A11-2a 351 H NH Aril R11-1 313 H NH Ar9 A11-2b 352 H NH Aril R11-2 314 H NH Ar9 A11-3a 353 H NH Aril R11-3 315 H NH Ar9 A11-3b 354 H NH Aril R11-4 316 H NH Arlo R11-1 355 H NH Aril R11-5 317 H NH Arlo R11-2 356 H NH Aril R11-6 318 H NH Arlo R11-3 357 H NH Aril R11-7 319 H NH Arlo R11-4 358 H NH Aril R11-8 320 H NH Arlo R11-5 359 H NH Aril R11-9 321 H NH Arlo R11-6 360 H NH Aril R11-10 322 H NH Arlo R11-7 361 H NH Aril R11-11 323 H NH Arlo R11-8 362 H NH Aril R11-12 324 H NH Arlo R11-9 363 H NH Aril R11-13 325 H NH Arlo R11-10 364 H NH Aril R11-14 326 H NH Arlo R11-11 365 H NH Aril R11-15 327 H NH Arlo R11-12 366 H NH Aril R11-16 328 H NH Arlo R11-13 367 H NH Aril R11-17 329 H NH Arlo R11-14 368 H NH Aril R11-18 330 H NH Arlo R11-15 369 H NH Aril R11-19 331 H NH Arl R11-16 370 H NH Aril R11-20 332 H NH Arlo R11-17 371 H NH Aril R11-21 333 H NH Arlo R11-18 372 H NH Aril R11-22 334 H NH Arl R11-19 373 H NH Aril R11-23 335 H NH Arl R11-20 374 H NH Aril R11-24 336 H NH Arl R11-21 375 H NH Aril R11-25 337 H NH Arlo R11-22 376 H NH Aril R11-26 338 H NH Arl R11-23 377 H NH Aril R11-27 339 H NH Arl R11-24 378 H NH Aril R11-28 340 H NH Arlo R11-25 379 H NH Aril R11-29 341 H NH Arlo R11-26 380 H NH Aril A11-la 342 H NH Arlo R11-27 381 H NH Aril A11-lb 343 H NH Arlo R11-28 382 H NH Aril A11-2a Line R Q Ar D Line R Q Ar D
383 H NH Aril A11-2b 422 H NCH3 Arl R11-2 384 H NH Aril A11-3a 423 H NCH3 Arl R11-3 385 H NH Aril A11-3b 424 H NCH3 Arl R11-4 386 H NH Ar12 R11-1 425 H NCH3 Arl R11-5 387 H NH Ar12 R11-2 426 H NCH3 Arl R11-6 388 H NH Ar12 R11-3 427 H NCH3 Arl R11-7 389 H NH Ar12 R11-4 428 H NCH3 Arl R11-8 390 H NH Ar12 R11-5 429 H NCH3 Arl R11-9 391 H NH Ar12 R11-6 430 H NCH3 Arl R11-10 392 H NH Ar12 R11-7 431 H NCH3 Arl R11-11 393 H NH Ar12 R11-8 432 H NCH3 Arl R11-12 394 H NH Ar12 R11-9 433 H NCH3 Arl R11-13 395 H NH Ar12 R11-10 434 H NCH3 Arl R11-14 396 H NH Ar12 R11-11 435 H NCH3 Arl R11-15 397 H NH Ar12 R11-12 436 H NCH3 Arl R11-16 398 H NH Ar12 R11-13 437 H NCH3 Arl R11-17 399 H NH Ar12 R11-14 438 H NCH3 Arl R11-18 400 H NH Ar12 R11-15 439 H NCH3 Arl R11-19 401 H NH Ar12 R11-16 440 H NCH3 Arl R11-20 402 H NH Ar12 R11-17 441 H NCH3 Arl R11-21 403 H NH Ar12 R11-18 442 H NCH3 Arl R11-22 404 H NH Ar12 R11-19 443 H NCH3 Arl R11-23 405 H NH Ar12 R11-20 444 H NCH3 Arl R11-24 406 H NH Ar12 R11-21 445 H NCH3 Arl R11-25 407 H NH Ar12 R11-22 446 H NCH3 Arl R11-26 408 H NH Ar12 R11-23 447 H NCH3 Arl R11-27 409 H NH Ar12 R11-24 448 H NCH3 Arl R11-28 410 H NH Ar12 R11-25 449 H NCH3 Arl R11-29 411 H NH Ar12 R11-26 450 H NCH3 Arl A11-la 412 H NH Ar12 R11-27 451 H NCH3 Arl A11-lb 413 H NH Ar12 R11-28 452 H NCH3 Arl A11-2a 414 H NH Ar12 R11-29 453 H NCH3 Arl A11-2b 415 H NH Ar12 A11-la 454 H NCH3 Arl A11-3a 416 H NH Ar12 A11-lb 455 H NCH3 Arl A11-3b 417 H NH Ar12 A11-2a 456 H NCH3 Ar2 R11-1 418 H NH Ar12 A11-2b 457 H NCH3 Ar2 R11-2 419 H NH Ar12 A11-3a 458 H NCH3 Ar2 R11-3 420 H NH Ar12 A11-3b 459 H NCH3 Ar2 R11-4 421 H NCH3 Arl R11-1 460 H NCH3 Ar2 R11-5 Line R Q Ar D Line R Q Ar D
461 H NCH3 Ar2 R11-6 500 H NCH3 Ar3 R11-10 462 H NCH3 Ar2 R11-7 501 H NCH3 Ar3 R11-11 463 H NCH3 Ar2 R11-8 502 H NCH3 Ar3 R11-12 464 H NCH3 Ar2 R11-9 503 H NCH3 Ar3 R11-13 465 H NCH3 Ar2 R11-10 504 H NCH3 Ar3 R11-14 466 H NCH3 Ar2 R11-11 505 H NCH3 Ar3 R11-15 467 H NCH3 Ar2 R11-12 506 H NCH3 Ar3 R11-16 468 H NCH3 Ar2 R11-13 507 H NCH3 Ar3 R11-17 469 H NCH3 Ar2 R11-14 508 H NCH3 Ar3 R11-18 470 H NCH3 Ar2 R11-15 509 H NCH3 Ar3 R11-19 471 H NCH3 Ar2 R11-16 510 H NCH3 Ar3 R11-20 472 H NCH3 Ar2 R11-17 511 H NCH3 Ar3 R11-21 473 H NCH3 Ar2 R11-18 512 H NCH3 Ar3 R11-22 474 H NCH3 Ar2 R11-19 513 H NCH3 Ar3 R11-23 475 H NCH3 Ar2 R11-20 514 H NCH3 Ar3 R11-24 476 H NCH3 Ar2 R11-21 515 H NCH3 Ar3 R11-25 477 H NCH3 Ar2 R11-22 516 H NCH3 Ar3 R11-26 478 H NCH3 Ar2 R11-23 517 H NCH3 Ar3 R11-27 479 H NCH3 Ar2 R11-24 518 H NCH3 Ar3 R11-28 480 H NCH3 Ar2 R11-25 519 H NCH3 Ar3 R11-29 481 H NCH3 Ar2 R11-26 520 H NCH3 Ar3 A11-la 482 H NCH3 Ar2 R11-27 521 H NCH3 Ar3 A11-lb 483 H NCH3 Ar2 R11-28 522 H NCH3 Ar3 A11-2a 484 H NCH3 Ar2 R11-29 523 H NCH3 Ar3 A11-2b 485 H NCH3 Ar2 A11-la 524 H NCH3 Ar3 A11-3a 486 H NCH3 Ar2 A11-1b 525 H NCH3 Ar4 A11-3b 487 H NCH3 Ar2 A11-2a 526 H NCH3 Ar4 R11-1 488 H NCH3 Ar2 A11-2b 527 H NCH3 Ar4 R11-2 489 H NCH3 Ar2 A11-3a 528 H NCH3 Ar4 R11-3 490 H NCH3 Ar2 A11-3b 529 H NCH3 Ar4 R11-4 491 H NCH3 Ar3 R11-1 530 H NCH3 Ar4 R11-5 492 H NCH3 Ar3 R11-2 531 H NCH3 Ar4 R11-6 493 H NCH3 Ar3 R11-3 532 H NCH3 Ar4 R11-7 494 H NCH3 Ar3 R11-4 533 H NCH3 Ar4 R11-8 495 H NCH3 Ar3 R11-5 534 H NCH3 Ar4 R11-9 496 H NCH3 Ar3 R11-6 535 H NCH3 Ar4 R11-10 497 H NCH3 Ar3 R11-7 536 H NCH3 Ar4 R11-11 498 H NCH3 Ar3 R11-8 537 H NCH3 Ar4 R11-12 499 H NCH3 Ar3 R11-9 538 H NCH3 Ar4 R11-13 Line R Q Ar D Line R Q Ar D
539 H NCH3 AO R11-14 578 H NCH3 Ar5 R11-18 540 H NCH3 AO R11-15 579 H NCH3 Ar5 R11-19 541 H NCH3 Art R11-16 580 H NCH3 Ar5 R11-20 542 H NCH3 Art R11-17 581 H NCH3 Ar5 R11-21 543 H NCH3 AO R11-18 582 H NCH3 Ar5 R11-22 544 H NCH3 Art R11-19 583 H NCH3 Ar5 R11-23 545 H NCH3 Art R11-20 584 H NCH3 Ar5 R11-24 546 H NCH3 Art R11-21 585 H NCH3 Ar5 R11-25 547 H NCH3 Art R11-22 586 H NCH3 Ar5 R11-26 548 H NCH3 Art R11-23 587 H NCH3 Ar5 R11-27 549 H NCH3 Art R11-24 588 H NCH3 Ar5 R11-28 550 H NCH3 Art R11-25 589 H NCH3 Ar5 R11-29 551 H NCH3 Art R11-26 590 H NCH3 Ar5 A11-la 552 H NCH3 Art R11-27 591 H NCH3 Ar5 A11-lb 553 H NCH3 Art R11-28 592 H NCH3 Ar5 A11-2a 554 H NCH3 Art R11-29 593 H NCH3 Ar5 A11-2b 555 H NCH3 Art A11-la 594 H NCH3 Ar5 A11-3a 556 H NCH3 Art A11-1b 595 H NCH3 Ar5 A11-3b 557 H NCH3 Art A11-2a 596 H NCH3 Ar6 R11-1 558 H NCH3 Art A11-2b 597 H NCH3 Ar6 R11-2 559 H NCH3 Art A11-3a 598 H NCH3 Ar6 R11-3 560 H NCH3 Art A11-3b 599 H NCH3 Ar6 R11-4 561 H NCH3 Ar5 R11-1 600 H NCH3 Ar6 R11-5 562 H NCH3 Ar5 R11-2 601 H NCH3 Ar6 R11-6 563 H NCH3 Ar5 R11-3 602 H NCH3 Ar6 R11-7 564 H NCH3 Ar5 R11-4 603 H NCH3 Ar6 R11-8 565 H NCH3 Ar5 R11-5 604 H NCH3 Ar6 R11-9 566 H NCH3 Ar5 R11-6 605 H NCH3 Ar6 R11-10 567 H NCH3 Ar5 R11-7 606 H NCH3 Ar6 R11-11 568 H NCH3 Ar5 R11-8 607 H NCH3 Ar6 R11-12 569 H NCH3 Ar5 R11-9 608 H NCH3 Ar6 R11-13 570 H NCH3 Ar5 R11-10 609 H NCH3 Ar6 R11-14 571 H NCH3 Ar5 R11-11 610 H NCH3 Ar6 R11-15 572 H NCH3 Ar5 R11-12 611 H NCH3 Ar6 R11-16 573 H NCH3 Ar5 R11-13 612 H NCH3 Ar6 R11-17 574 H NCH3 Ar5 R11-14 613 H NCH3 Ar6 R11-18 575 H NCH3 Ar5 R11-15 614 H NCH3 Ar6 R11-19 576 H NCH3 Ar5 R11-16 615 H NCH3 Ar6 R11-20 577 H NCH3 Ar5 R11-17 616 H NCH3 Ar6 R11-21 Line R Q Ar D Line R Q Ar D
617 H NCH3 Ar6 R11-22 656 H NCH3 AC R11-26 618 H NCH3 Ar6 R11-23 657 H NCH3 AC R11-27 619 H NCH3 Ar6 R11-24 658 H NCH3 Ar7 R11-28 620 H NCH3 Ar6 R11-25 659 H NCH3 Ar7 R11-29 621 H NCH3 Ar6 R11-26 660 H NCH3 AC A11-la 622 H NCH3 Ar6 R11-27 661 H NCH3 Ar7 A11-lb 623 H NCH3 Ar6 R11-28 662 H NCH3 Ar7 A11-2a 624 H NCH3 Ar6 R11-29 663 H NCH3 Ar7 A11-2b 625 H NCH3 Ar6 A11-la 664 H NCH3 Ar7 A11-3a 626 H NCH3 Ar6 A11-lb 665 H NCH3 Ar7 A11-3b 627 H NCH3 Ar6 A11-2a 666 H NCH3 Ar8 R11-1 628 H NCH3 Ar6 A11-2b 667 H NCH3 Ar8 R11-2 629 H NCH3 Ar6 A11-3a 668 H NCH3 Ar8 R11-3 630 H NCH3 Ar6 A11-3b 669 H NCH3 Ar8 R11-4 631 H NCH3 Ar7 R11-1 670 H NCH3 Ar8 R11-5 632 H NCH3 Ar7 R11-2 671 H NCH3 Ar8 R11-6 633 H NCH3 Ar7 R11-3 672 H NCH3 Ar8 R11-7 634 H NCH3 Ar7 R11-4 673 H NCH3 Ar8 R11-8 635 H NCH3 Ar7 R11-5 674 H NCH3 Ar8 R11-9 636 H NCH3 Ar7 R11-6 675 H NCH3 Ar8 R11-10 637 H NCH3 Ar7 R11-7 676 H NCH3 Ar8 R11-11 638 H NCH3 Ar7 R11-8 677 H NCH3 Ar8 R11-12 639 H NCH3 Ar7 R11-9 678 H NCH3 Ar8 R11-13 640 H NCH3 Ar7 R11-10 679 H NCH3 Ar8 R11-14 641 H NCH3 Ar7 R11-11 680 H NCH3 Ar8 R11-15 642 H NCH3 Ar7 R11-12 681 H NCH3 Ar8 R11-16 644 H NCH3 Ar7 R11-14 683 H NCH3 Ar8 R11-18 645 H NCH3 Ar7 R11-15 684 H NCH3 Ar8 R11-19 649 H NCH3 Ar7 R11-19 688 H NCH3 Ar8 R11-23 652 H NCH3 Ar7 R11-22 691 H NCH3 Ar8 R11-26 653 H NCH3 Ar7 R11-23 692 H NCH3 Ar8 R11-27 654 H NCH3 Ar7 R11-24 693 H NCH3 Ar8 R11-28 655 H NCH3 Ar7 R11-25 694 H NCH3 Ar8 R11-29 Line R Q Ar D Line R Q Ar D
695 H NCH3 Ar8 A11-la 734 H NCH3 Ar9 A11-3a 696 H NCH3 Ar8 A11-1b 735 H NCH3 Ar9 A11-3b 697 H NCH3 Ar8 A11-2a 736 H NCH3 Arlo R11-1 698 H NCH3 Ar8 A11-2b 737 H NCH3 Arlo R11-2 699 H NCH3 Ar8 A11-3a 738 H NCH3 Arl R11-3 700 H NCH3 Ar8 A11-3b 739 H NCH3 Arlo R11-4 701 H NCH3 Ar9 R11-1 740 H NCH3 Arlo R11-5 702 H NCH3 Ar9 R11-2 741 H NCH3 Arlo R11-6 703 H NCH3 Ar9 R11-3 742 H NCH3 Arlo R11-7 704 H NCH3 Ar9 R11-4 743 H NCH3 Arlo R11-8 705 H NCH3 Ar9 R11-5 744 H NCH3 Arlo R11-9 706 H NCH3 Ar9 R11-6 745 H NCH3 Arlo R11-10 707 H NCH3 Ar9 R11-7 746 H NCH3 Arlo R11-11 708 H NCH3 Ar9 R11-8 747 H NCH3 Arlo R11-12 709 H NCH3 Ar9 R11-9 748 H NCH3 Arlo R11-13 710 H NCH3 Ar9 R11-10 749 H NCH3 Arlo R11-14 711 H NCH3 Ar9 R11-11 750 H NCH3 Arlo R11-15 712 H NCH3 Ar9 R11-12 751 H NCH3 Arlo R11-16 713 H NCH3 Ar9 R11-13 752 H NCH3 Arlo R11-17 714 H NCH3 Ar9 R11-14 753 H NCH3 Arlo R11-18 715 H NCH3 Ar9 R11-15 754 H NCH3 Arlo R11-19 716 H NCH3 Ar9 R11-16 755 H NCH3 Arlo R11-20 717 H NCH3 Ar9 R11-17 756 H NCH3 Arlo R11-21 718 H NCH3 Ar9 R11-18 757 H NCH3 Arlo R11-22 719 H NCH3 Ar9 R11-19 758 H NCH3 Arlo R11-23 720 H NCH3 Ar9 R11-20 759 H NCH3 Arlo R11-24 721 H NCH3 Ar9 R11-21 760 H NCH3 Arl R11-25 722 H NCH3 Ar9 R11-22 761 H NCH3 Arlo R11-26 723 H NCH3 Ar9 R11-23 762 H NCH3 Arlo R11-27 724 H NCH3 Ar9 R11-24 763 H NCH3 Arl R11-28 725 H NCH3 Ar9 R11-25 764 H NCH3 Arl R11-29 726 H NCH3 Ar9 R11-26 765 H NCH3 Arl A11-la 727 H NCH3 Ar9 R11-27 766 H NCH3 Arlo A11-lb 728 H NCH3 Ar9 R11-28 767 H NCH3 Arl A11-2a 729 H NCH3 Ar9 R11-29 768 H NCH3 Arl A11-2b 730 H NCH3 Ar9 A11-la 769 H NCH3 Arlo A11-3a 731 H NCH3 Ar9 A11-lb 770 H NCH3 Arlo A11-3b 732 H NCH3 Ar9 A11-2a 771 H NCH3 Aril R11-1 733 H NCH3 Ar9 A11-2b 772 H NCH3 Aril R11-2 Line R Q Ar D Line R Q Ar D
773 H NCH3 Aril R11-3 812 H NCH3 Ar12 R11-7 774 H NCH3 Aril R11-4 813 H NCH3 Ar12 R11-8 775 H NCH3 Aril R11-5 814 H NCH3 Ar12 R11-9 776 H NCH3 Aril R11-6 815 H NCH3 Ar12 R11-10 777 H NCH3 Aril R11-7 816 H NCH3 Ar12 R11-11 778 H NCH3 Aril R11-8 817 H NCH3 Ar12 R11-12 779 H NCH3 Aril R11-9 818 H NCH3 Ar12 R11-13 780 H NCH3 Aril R11-10 819 H NCH3 Ar12 R11-14 781 H NCH3 Aril R11-11 820 H NCH3 Ar12 R11-15 782 H NCH3 Aril R11-12 821 H NCH3 Ar12 R11-16 783 H NCH3 Aril R11-13 822 H NCH3 Ar12 R11-17 784 H NCH3 Aril R11-14 823 H NCH3 Ar12 R11-18 785 H NCH3 Aril R11-15 824 H NCH3 Ar12 R11-19 786 H NCH3 Aril R11-16 825 H NCH3 Ar12 R11-20 787 H NCH3 Aril R11-17 826 H NCH3 Ar12 R11-21 788 H NCH3 Aril R11-18 827 H NCH3 Ar12 R11-22 789 H NCH3 Aril R11-19 828 H NCH3 Ar12 R11-23 790 H NCH3 Aril R11-20 829 H NCH3 Ar12 R11-24 791 H NCH3 Aril R11-21 830 H NCH3 Ar12 R11-25 792 H NCH3 Aril R11-22 831 H NCH3 Ar12 R11-26 793 H NCH3 Aril R11-23 832 H NCH3 Ar12 R11-27 794 H NCH3 Aril R11-24 833 H NCH3 Ar12 R11-28 795 H NCH3 Aril R11-25 834 H NCH3 Ar12 R11-29 796 H NCH3 Aril R11-26 835 H NCH3 Ar12 A11-la 797 H NCH3 Aril R11-27 836 H NCH3 Ar12 A11-lb 798 H NCH3 Aril R11-28 837 H NCH3 Ar12 A11-2a 799 H NCH3 Aril R11-29 838 H NCH3 Ar12 A11-2b 800 H NCH3 Aril A11-la 839 H NCH3 Ar12 A11-3a 801 H NCH3 Aril A11-lb 840 H NCH3 Ar12 A11-3b 802 H NCH3 Aril A11-2a 841 H 0 Arl R11-1 803 H NCH3 Aril A11-2b 842 H 0 Arl R11-2 804 H NCH3 Aril A11-3a 843 H 0 Arl R11-3 805 H NCH3 Aril A11-3b 844 H 0 Arl R11-4 806 H NCH3 Ar12 R11-1 845 H 0 Arl R11-5 807 H NCH3 Ar12 R11-2 846 H 0 Arl R11-6 808 H NCH3 Ar12 R11-3 847 H 0 Arl R11-7 809 H NCH3 Ar12 R11-4 848 H 0 Arl R11-8 810 H NCH3 Ar12 R11-5 849 H 0 Arl R11-9 811 H NCH3 Ar12 R11-6 850 H 0 Arl R11-10 Line R Q Ar D Line R Q Ar D
851 H 0 Arl R11-11 890 H 0 Ar2 R11-15 852 H 0 Arl R11-12 891 H 0 Ar2 R11-16 853 H 0 Arl R11-13 892 H 0 Ar2 R11-17 854 H 0 Arl R11-14 893 H 0 Ar2 R11-18 855 H 0 Arl R11-15 894 H 0 Ar2 R11-19 856 H 0 Arl R11-16 895 H 0 Ar2 R11-20 857 H 0 Arl R11-17 896 H 0 Ar2 R11-21 858 H 0 Arl R11-18 897 H 0 Ar2 R11-22 859 H 0 Arl R11-19 898 H 0 Ar2 R11-23 860 H 0 Arl R11-20 899 H 0 Ar2 R11-24 861 H 0 Arl R11-21 900 H 0 Ar2 R11-25 862 H 0 Arl R11-22 901 H 0 Ar2 R11-26 863 H 0 Arl R11-23 902 H 0 Ar2 R11-27 864 H 0 Arl R11-24 903 H 0 Ar2 R11-28 865 H 0 Arl R11-25 904 H 0 Ar2 R11-29 866 H 0 Arl R11-26 905 H 0 Ar2 A11-la 867 H 0 Arl R11-27 906 H 0 Ar2 A11-lb 868 H 0 Arl R11-28 907 H 0 Ar2 A11-2a 869 H 0 Arl R11-29 908 H 0 Ar2 A11-2b 870 H 0 Arl A11-la 909 H 0 Ar2 A11-3a 871 H 0 Arl A11-1b 910 H 0 Ar2 A11-3b 872 H 0 Arl A11-2a 911 H 0 Ar3 R11-1 873 H 0 Arl A11-2b 912 H 0 Ar3 R11-2 874 H 0 Arl A11-3a 913 H 0 Ar3 R11-3 875 H 0 Arl A11-3b 914 H 0 Ar3 R11-4 876 H 0 Ar2 R11-1 915 H 0 Ar3 R11-5 877 H 0 Ar2 R11-2 916 H 0 Ar3 R11-6 878 H 0 Ar2 R11-3 917 H 0 Ar3 R11-7 879 H 0 Ar2 R11-4 918 H 0 Ar3 R11-8 880 H 0 Ar2 R11-5 919 H 0 Ar3 R11-9 881 H 0 Ar2 R11-6 920 H 0 Ar3 R11-10 882 H 0 Ar2 R11-7 921 H 0 Ar3 R11-11 883 H 0 Ar2 R11-8 922 H 0 Ar3 R11-12 884 H 0 Ar2 R11-9 923 H 0 Ar3 R11-13 885 H 0 Ar2 R11-10 924 H 0 Ar3 R11-14 886 H 0 Ar2 R11-11 925 H 0 Ar3 R11-15 887 H 0 Ar2 R11-12 926 H 0 Ar3 R11-16 888 H 0 Ar2 R11-13 927 H 0 Ar3 R11-17 889 H 0 Ar2 R11-14 928 H 0 Ar3 R11-18 Line R Q Ar D Line R Q Ar D
929 H 0 Ar3 R11-19 968 H 0 Ar4 R11-23 930 H 0 Ar3 R11-20 969 H 0 Ar4 R11-24 931 H 0 Ar3 R11-21 970 H 0 Ar4 R11-25 932 H 0 Ar3 R11-22 971 H 0 Ar4 R11-26 933 H 0 Ar3 R11-23 972 H 0 Ar4 R11-27 934 H 0 Ar3 R11-24 973 H 0 Ar4 R11-28 935 H 0 Ar3 R11-25 974 H 0 Ar4 R11-29 936 H 0 Ar3 R11-26 975 H 0 Ar4 A11-la 937 H 0 Ar3 R11-27 976 H 0 Ar4 A11-1b 938 H 0 Ar3 R11-28 977 H 0 Ar4 A11-2a 939 H 0 Ar3 R11-29 978 H 0 Ar4 A11-2b 940 H 0 Ar3 A11- 1 a 979 H 0 Ar4 A11-3a 941 H 0 Ar3 A11- 1 b 980 H 0 Ar4 A11-3b 942 H 0 Ar3 A11-2a 981 H 0 Ar5 R11-1 943 H 0 Ar3 A11-2b 982 H 0 Ar5 R11-2 944 H 0 Ar3 A11-3a 983 H 0 Ar5 R11-3 945 H 0 Art A11-3b 984 H 0 Ar5 R11-4 946 H 0 Art R11-1 985 H 0 Ar5 R11-5 947 H 0 Art R11-2 986 H 0 Ar5 R11-6 948 H 0 Art R11-3 987 H 0 Ar5 R11-7 949 H 0 Art R11-4 988 H 0 Ar5 R11-8 950 H 0 Art R11-5 989 H 0 Ar5 R11-9 951 H 0 Art R11-6 990 H 0 Ar5 R11-10 952 H 0 Art R11-7 991 H 0 Ar5 R11-11 953 H 0 Art R11-8 992 H 0 Ar5 R11-12 954 H 0 Art R11-9 993 H 0 Ar5 R11-13 955 H 0 AO R11-10 994 H 0 Ar5 R11-14 956 H 0 Art R11-11 995 H 0 Ar5 R11-15 957 H 0 Art R11-12 996 H 0 Ar5 R11-16 958 H 0 AO R11-13 997 H 0 Ar5 R11-17 959 H 0 AO R11-14 998 H 0 Ar5 R11-18 960 H 0 AO R11-15 999 H 0 Ar5 R11-19 961 H 0 Art R11-16 1000 H 0 Ar5 R11-20 962 H 0 AO R11-17 1001 H 0 Ar5 R11-21 963 H 0 AO R11-18 1002 H 0 Ar5 R11-22 964 H 0 Art R11-19 1003 H 0 Ar5 R11-23 965 H 0 Art R11-20 1004 H 0 Ar5 R11-24 966 H 0 Art R11-21 1005 H 0 Ar5 R11-25 967 H 0 Art R11-22 1006 H 0 Ar5 R11-26 Line R Q Ar D Line R Q Ar D
1007 H 0 Ar5 R11-27 1046 H 0 Ar6 A11-1b 1008 H 0 Ar5 R11-28 1047 H 0 Ar6 A11-2a 1009 H 0 Ar5 R11-29 1048 H 0 Ar6 A11-2b 1010 H 0 Ar5 A11-la 1049 H 0 Ar6 A11-3a 1011 H 0 Ar5 A11-lb 1050 H 0 Ar6 A11-3b 1012 H 0 Ar5 A11-2a 1051 H 0 Ar7 R11-1 1013 H 0 Ar5 A11-2b 1052 H 0 Ar7 R11-2 1014 H 0 Ar5 A11-3a 1053 H 0 Ar7 R11-3 1015 H 0 Ar5 A11-3b 1054 H 0 Ar7 R11-4 1016 H 0 Ar6 R11-1 1055 H 0 Ar7 R11-5 1017 H 0 Ar6 R11-2 1056 H 0 Ar7 R11-6 1018 H 0 Ar6 R11-3 1057 H 0 Ar7 R11-7 1019 H 0 Ar6 R11-4 1058 H 0 Ar7 R11-8 1020 H 0 Ar6 R11-5 1059 H 0 Ar7 R11-9 1021 H 0 Ar6 R11-6 1060 H 0 Ar7 R11-10 1022 H 0 Ar6 R11-7 1061 H 0 Ar7 R11-11 1023 H 0 Ar6 R11-8 1062 H 0 Ar7 R11-12 1024 H 0 Ar6 R11-9 1063 H 0 Ar7 R11-13 1025 H 0 Ar6 R11-10 1064 H 0 Ar7 R11-14 1026 H 0 Ar6 R11-11 1065 H 0 Ar7 R11-15 1027 H 0 Ar6 R11-12 1066 H 0 Ar7 R11-16 1028 H 0 Ar6 R11-13 1067 H 0 Ar7 R11-17 1029 H 0 Ar6 R11-14 1068 H 0 Ar7 R11-18 1030 H 0 Ar6 R11-15 1069 H 0 Ar7 R11-19 1031 H 0 Ar6 R11-16 1070 H 0 Ar7 R11-20 1032 H 0 Ar6 R11-17 1071 H 0 Ar7 R11-21 1033 H 0 Ar6 R11-18 1072 H 0 Ar7 R11-22 1034 H 0 Ar6 R11-19 1073 H 0 Ar7 R11-23 1035 H 0 Ar6 R11-20 1074 H 0 Ar7 R11-24 1036 H 0 Ar6 R11-21 1075 H 0 Ar7 R11-25 1037 H 0 Ar6 R11-22 1076 H 0 Ar7 R11-26 1038 H 0 Ar6 R11-23 1077 H 0 Ar7 R11-27 1039 H 0 Ar6 R11-24 1078 H 0 Ar7 R11-28 1040 H 0 Ar6 R11-25 1079 H 0 Ar7 R11-29 1041 H 0 Ar6 R11-26 1080 H 0 Ar7 A11-la 1042 H 0 Ar6 R11-27 1081 H 0 Ar7 A11-lb 1043 H 0 Ar6 R11-28 1082 H 0 Ar7 A11-2a 1044 H 0 Ar6 R11-29 1083 H 0 Ar7 A11-2b 1045 H 0 Ar6 A11- 1 a 1084 H 0 Ar7 A11-3a Line R Q Ar D Line R Q Ar D
1085 H 0 Ar7 A11-3b 1124 H 0 Ar9 R11-4 1086 H 0 Ar8 R11-1 1125 H 0 Ar9 R11-5 1087 H 0 Ar8 R11-2 1126 H 0 Ar9 R11-6 1088 H 0 Ar8 R11-3 1127 H 0 Ar9 R11-7 1089 H 0 Ar8 R11-4 1128 H 0 Ar9 R11-8 1090 H 0 Ar8 R11-5 1129 H 0 Ar9 R11-9 1091 H 0 Ar8 R11-6 1130 H 0 Ar9 R11-10 1092 H 0 Ar8 R11-7 1131 H 0 Ar9 R11-11 1093 H 0 Ar8 R11-8 1132 H 0 Ar9 R11-12 1094 H 0 Ar8 R11-9 1133 H 0 Ar9 R11-13 1095 H 0 Ar8 R11-10 1134 H 0 Ar9 R11-14 1096 H 0 Ar8 R11-11 1135 H 0 Ar9 R11-15 1097 H 0 Ar8 R11-12 1136 H 0 Ar9 R11-16 1098 H 0 Ar8 R11-13 1137 H 0 Ar9 R11-17 1099 H 0 Ar8 R11-14 1138 H 0 Ar9 R11-18 1100 H 0 Ar8 R11-15 1139 H 0 Ar9 R11-19 1101 H 0 Ar8 R11-16 1140 H 0 Ar9 R11-20 1102 H 0 Ar8 R11-17 1141 H 0 Ar9 R11-21 1103 H 0 Ar8 R11-18 1142 H 0 Ar9 R11-22 1104 H 0 Ar8 R11-19 1143 H 0 Ar9 R11-23 1105 H 0 Ar8 R11-20 1144 H 0 Ar9 R11-24 1106 H 0 Ar8 R11-21 1145 H 0 Ar9 R11-25 1107 H 0 Ar8 R11-22 1146 H 0 Ar9 R11-26 1108 H 0 Ar8 R11-23 1147 H 0 Ar9 R11-27 1109 H 0 Ar8 R11-24 1148 H 0 Ar9 R11-28 1110 H 0 Ar8 R11-25 1149 H 0 Ar9 R11-29 1111 H 0 Ar8 R11-26 1150 H 0 Ar9 A11-la 1112 H 0 Ar8 R11-27 1151 H 0 Ar9 A11-lb 1113 H 0 Ar8 R11-28 1152 H 0 Ar9 A11-2a 1114 H 0 Ar8 R11-29 1153 H 0 Ar9 A11-2b 1115 H 0 Ar8 A11-la 1154 H 0 Ar9 A11-3a 1116 H 0 Ar8 A11-lb 1155 H 0 Ar9 A11-3b 1117 H 0 Ar8 A11-2a 1156 H 0 Arlo R11-1 1118 H 0 Ar8 A11-2b 1157 H 0 Arl R11-2 1119 H 0 Ar8 A11-3a 1158 H 0 Arl R11-3 1120 H 0 Ar8 A11-3b 1159 H 0 Arlo R11-4 1121 H 0 Ar9 R11-1 1160 H 0 Arlo R11-5 1122 H 0 Ar9 R11-2 1161 H 0 Arlo R11-6 1123 H 0 Ar9 R11-3 1162 H 0 Arlo R11-7 Line R Q Ar D Line R Q Ar D
1163 H 0 Arl R11-8 1202 H 0 Aril R11-12 1164 H 0 Arl R11-9 1203 H 0 Aril R11-13 1165 H 0 Arlo R11-10 1204 H 0 Aril R11-14 1166 H 0 Arlo R11-11 1205 H 0 Aril R11-15 1167 H 0 Arl R11-12 1206 H 0 Aril R11-16 1168 H 0 Arlo R11-13 1207 H 0 Aril R11-17 1169 H 0 Arlo R11-14 1208 H 0 Aril R11-18 1170 H 0 Arlo R11-15 1209 H 0 Aril R11-19 1171 H 0 Arlo R11-16 1210 H 0 Aril R11-20 1172 H 0 Arlo R11-17 1211 H 0 Aril R11-21 1173 H 0 Arlo R11-18 1212 H 0 Aril R11-22 1174 H 0 Arlo R11-19 1213 H 0 Aril R11-23 1175 H 0 Arlo R11-20 1214 H 0 Aril R11-24 1176 H 0 Arlo R11-21 1215 H 0 Aril R11-25 1177 H 0 Arlo R11-22 1216 H 0 Aril R11-26 1178 H 0 Arlo R11-23 1217 H 0 Aril R11-27 1179 H 0 Arlo R11-24 1218 H 0 Aril R11-28 1180 H 0 Arlo R11-25 1219 H 0 Aril R11-29 1181 H 0 Arlo R11-26 1220 H 0 Aril A11-la 1182 H 0 Arlo R11-27 1221 H 0 Aril A11-lb 1183 H 0 Arlo R11-28 1222 H 0 Aril A11-2a 1184 H 0 Arlo R11-29 1223 H 0 Aril A11-2b 1185 H 0 Arlo A11-la 1224 H 0 Aril A11-3a 1186 H 0 Arlo A11-lb 1225 H 0 Aril A11-3b 1187 H 0 Arlo A11-2a 1226 H 0 Ar12 R11-1 1188 H 0 Arlo A11-2b 1227 H 0 Ar12 R11-2 1189 H 0 Arl A11-3a 1228 H 0 Ar12 R11-3 1190 H 0 Arlo A11-3b 1229 H 0 Ar12 R11-4 1191 H 0 Aril R11-1 1230 H 0 Ar12 R11-5 1192 H 0 Aril R11-2 1231 H 0 Ar12 R11-6 1193 H 0 Aril R11-3 1232 H 0 Ar12 R11-7 1194 H 0 Aril R11-4 1233 H 0 Ar12 R11-8 1195 H 0 Aril R11-5 1234 H 0 Ar12 R11-9 1196 H 0 Aril R11-6 1235 H 0 Ar12 R11-10 1197 H 0 Aril R11-7 1236 H 0 Ar12 R11-11 1198 H 0 Aril R11-8 1237 H 0 Ar12 R11-12 1199 H 0 Aril R11-9 1238 H 0 Ar12 R11-13 1200 H 0 Aril R11-10 1239 H 0 Ar12 R11-14 1201 H 0 Aril R11-11 1240 H 0 Ar12 R11-15 Line R Q Ar D Line R Q Ar D
1241 H 0 Ar12 R11-16 1280 CH3 NH Arl R11-20 1242 H 0 Ar12 R11-17 1281 CH3 NH Arl R11-21 1243 H 0 Ar12 R11-18 1282 CH3 NH Arl R11-22 1244 H 0 Ar12 R11-19 1283 CH3 NH Arl R11-23 1245 H 0 Ar12 R11-20 1284 CH3 NH Arl R11-24 1246 H 0 Ar12 R11-21 1285 CH3 NH Arl R11-25 1247 H 0 Ar12 R11-22 1286 CH3 NH Arl R11-26 1248 H 0 Ar12 R11-23 1287 CH3 NH Arl R11-27 1249 H 0 Ar12 R11-24 1288 CH3 NH Arl R11-28 1250 H 0 Ar12 R11-25 1289 CH3 NH Arl R11-29 1251 H 0 Ar12 R11-26 1290 CH3 NH Arl A11-la 1252 H 0 Ar12 R11-27 1291 CH3 NH Arl A11-lb 1253 H 0 Ar12 R11-28 1292 CH3 NH Arl A11-2a 1254 H 0 Ar12 R11-29 1293 CH3 NH Arl A11-2b 1255 H 0 Ar12 A11-la 1294 CH3 NH Arl A11-3a 1256 H 0 Ar12 A11-lb 1295 CH3 NH Arl A11-3b 1257 H 0 Ar12 A11-2a 1296 CH3 NH Ar2 R11-1 1258 H 0 Ar12 A11-2b 1297 CH3 NH Ar2 R11-2 1259 H 0 Ar12 A11-3a 1298 CH3 NH Ar2 R11-3 1260 H 0 Ar12 A11-3b 1299 CH3 NH Ar2 R11-4 1261 CH3 NH Arl R11-1 1300 CH3 NH Ar2 R11-5 1262 CH3 NH Arl R11-2 1301 CH3 NH Ar2 R11-6 1263 CH3 NH Arl R11-3 1302 CH3 NH Ar2 R11-7 1264 CH3 NH Arl R11-4 1303 CH3 NH Ar2 R11-8 1265 CH3 NH Arl R11-5 1304 CH3 NH Ar2 R11-9 1266 CH3 NH Arl R11-6 1305 CH3 NH Ar2 R11-10 1267 CH3 NH Arl R11-7 1306 CH3 NH Ar2 R11-11 1268 CH3 NH Arl R11-8 1307 CH3 NH Ar2 R11-12 1269 CH3 NH Arl R11-9 1308 CH3 NH Ar2 R11-13 1270 CH3 NH Arl R11-10 1309 CH3 NH Ar2 R11-14 1271 CH3 NH Arl R11-11 1310 CH3 NH Ar2 R11-15 1272 CH3 NH Arl R11-12 1311 CH3 NH Ar2 R11-16 1273 CH3 NH Arl R11-13 1312 CH3 NH Ar2 R11-17 1274 CH3 NH Arl R11-14 1313 CH3 NH Ar2 R11-18 1275 CH3 NH Arl R11-15 1314 CH3 NH Ar2 R11-19 1276 CH3 NH Arl R11-16 1315 CH3 NH Ar2 R11-20 1277 CH3 NH Arl R11-17 1316 CH3 NH Ar2 R11-21 1278 CH3 NH Arl R11-18 1317 CH3 NH Ar2 R11-22 1279 CH3 NH Arl R11-19 1318 CH3 NH Ar2 R11-23 Line R Q Ar D Line R Q Ar D
1319 CH3 NH Ar2 R11-24 1358 CH3 NH Ar3 R11-28 1320 CH3 NH Ar2 R11-25 1359 CH3 NH Ar3 R11-29 1321 CH3 NH Ar2 R11-26 1360 CH3 NH Ar3 A11-la 1322 CH3 NH Ar2 R11-27 1361 CH3 NH Ar3 A11-lb 1323 CH3 NH Ar2 R11-28 1362 CH3 NH Ar3 A11-2a 1324 CH3 NH Ar2 R11-29 1363 CH3 NH Ar3 A11-2b 1325 CH3 NH Ar2 A11-la 1364 CH3 NH Ar3 A11-3a 1326 CH3 NH Ar2 A11-lb 1365 CH3 NH Art A11-3b 1327 CH3 NH Ar2 A11-2a 1366 CH3 NH Art R11-1 1328 CH3 NH Ar2 A11-2b 1367 CH3 NH Art R11-2 1329 CH3 NH Ar2 A11-3a 1368 CH3 NH Art R11-3 1330 CH3 NH Ar2 A11-3b 1369 CH3 NH Art R11-4 1331 CH3 NH Ar3 R11-1 1370 CH3 NH Art R11-5 1332 CH3 NH Ar3 R11-2 1371 CH3 NH Art R11-6 1333 CH3 NH Ar3 R11-3 1372 CH3 NH Art R11-7 1334 CH3 NH Ar3 R11-4 1373 CH3 NH Art R11-8 1335 CH3 NH Ar3 R11-5 1374 CH3 NH Art R11-9 1336 CH3 NH Ar3 R11-6 1375 CH3 NH Art R11-10 1337 CH3 NH Ar3 R11-7 1376 CH3 NH Art R11-11 1338 CH3 NH Ar3 R11-8 1377 CH3 NH Art R11-12 1339 CH3 NH Ar3 R11-9 1378 CH3 NH Art R11-13 1340 CH3 NH Ar3 R11-10 1379 CH3 NH Art R11-14 1341 CH3 NH Ar3 R11-11 1380 CH3 NH Art R11-15 1342 CH3 NH Ar3 R11-12 1381 CH3 NH Art R11-16 1343 CH3 NH Ar3 R11-13 1382 CH3 NH Art R11-17 1344 CH3 NH Ar3 R11-14 1383 CH3 NH Art R11-18 1345 CH3 NH Ar3 R11-15 1384 CH3 NH AO R11-19 1346 CH3 NH Ar3 R11-16 1385 CH3 NH Art R11-20 1347 CH3 NH Ar3 R11-17 1386 CH3 NH Art R11-21 1348 CH3 NH Ar3 R11-18 1387 CH3 NH AO R11-22 1349 CH3 NH Ar3 R11-19 1388 CH3 NH AO R11-23 1350 CH3 NH Ar3 R11-20 1389 CH3 NH AO R11-24 1351 CH3 NH Ar3 R11-21 1390 CH3 NH Art R11-25 1352 CH3 NH Ar3 R11-22 1391 CH3 NH AO R11-26 1353 CH3 NH Ar3 R11-23 1392 CH3 NH AO R11-27 1354 CH3 NH Ar3 R11-24 1393 CH3 NH Art R11-28 1355 CH3 NH Ar3 R11-25 1394 CH3 NH Art R11-29 1356 CH3 NH Ar3 R11-26 1395 CH3 NH Art A11-la 1357 CH3 NH Ar3 R11-27 1396 CH3 NH Art A11-lb Line R Q Ar D Line R Q Ar D
1397 CH3 NH AO A11-2a 1436 CH3 NH Ar6 R11-1 1398 CH3 NH AO A11-2b 1437 CH3 NH Ar6 R11-2 1399 CH3 NH Art A11-3a 1438 CH3 NH Ar6 R11-3 1400 CH3 NH Art A11-3b 1439 CH3 NH Ar6 R11-4 1401 CH3 NH Ar5 R11-1 1440 CH3 NH Ar6 R11-5 1402 CH3 NH Ar5 R11-2 1441 CH3 NH Ar6 R11-6 1403 CH3 NH Ar5 R11-3 1442 CH3 NH Ar6 R11-7 1404 CH3 NH Ar5 R11-4 1443 CH3 NH Ar6 R11-8 1405 CH3 NH Ar5 R11-5 1444 CH3 NH Ar6 R11-9 1406 CH3 NH Ar5 R11-6 1445 CH3 NH Ar6 R11-10 1407 CH3 NH Ar5 R11-7 1446 CH3 NH Ar6 R11-11 1408 CH3 NH Ar5 R11-8 1447 CH3 NH Ar6 R11-12 1409 CH3 NH Ar5 R11-9 1448 CH3 NH Ar6 R11-13 1410 CH3 NH Ar5 R11-10 1449 CH3 NH Ar6 R11-14 1411 CH3 NH Ar5 R11-11 1450 CH3 NH Ar6 R11-15 1412 CH3 NH Ar5 R11-12 1451 CH3 NH Ar6 R11-16 1413 CH3 NH Ar5 R11-13 1452 CH3 NH Ar6 R11-17 1414 CH3 NH Ar5 R11-14 1453 CH3 NH Ar6 R11-18 1415 CH3 NH Ar5 R11-15 1454 CH3 NH Ar6 R11-19 1416 CH3 NH Ar5 R11-16 1455 CH3 NH Ar6 R11-20 1417 CH3 NH Ar5 R11-17 1456 CH3 NH Ar6 R11-21 1418 CH3 NH Ar5 R11-18 1457 CH3 NH Ar6 R11-22 1419 CH3 NH Ar5 R11-19 1458 CH3 NH Ar6 R11-23 1420 CH3 NH Ar5 R11-20 1459 CH3 NH Ar6 R11-24 1421 CH3 NH Ar5 R11-21 1460 CH3 NH Ar6 R11-25 1422 CH3 NH Ar5 R11-22 1461 CH3 NH Ar6 R11-26 1423 CH3 NH Ar5 R11-23 1462 CH3 NH Ar6 R11-27 1424 CH3 NH Ar5 R11-24 1463 CH3 NH Ar6 R11-28 1425 CH3 NH Ar5 R11-25 1464 CH3 NH Ar6 R11-29 1426 CH3 NH Ar5 R11-26 1465 CH3 NH Ar6 A11-la 1427 CH3 NH Ar5 R11-27 1466 CH3 NH Ar6 A11-lb 1428 CH3 NH Ar5 R11-28 1467 CH3 NH Ar6 A11-2a 1429 CH3 NH Ar5 R11-29 1468 CH3 NH Ar6 A11-2b 1430 CH3 NH Ar5 A11-la 1469 CH3 NH Ar6 A11-3a 1431 CH3 NH Ar5 A11-lb 1470 CH3 NH Ar6 A11-3b 1432 CH3 NH Ar5 A11-2a 1471 CH3 NH Ar7 R11-1 1433 CH3 NH Ar5 A11-2b 1472 CH3 NH Ar7 R11-2 1434 CH3 NH Ar5 A11-3a 1473 CH3 NH Ar7 R11-3 1435 CH3 NH Ar5 A11-3b 1474 CH3 NH Ar7 R11-4 Line R Q Ar D Line R Q Ar D
1475 CH3 NH AC R11-5 1514 CH3 NH Ar8 R11-9 1476 CH3 NH AC R11-6 1515 CH3 NH Ar8 R11-10 1477 CH3 NH Ar7 R11-7 1516 CH3 NH Ar8 R11-11 1478 CH3 NH Ar7 R11-8 1517 CH3 NH Ar8 R11-12 1479 CH3 NH AC R11-9 1518 CH3 NH Ar8 R11-13 1480 CH3 NH Ar7 R11-10 1519 CH3 NH Ar8 R11-14 1481 CH3 NH Ar7 R11-11 1520 CH3 NH Ar8 R11-15 1482 CH3 NH Ar7 R11-12 1521 CH3 NH Ar8 R11-16 1483 CH3 NH Ar7 R11-13 1522 CH3 NH Ar8 R11-17 1484 CH3 NH Ar7 R11-14 1523 CH3 NH Ar8 R11-18 1485 CH3 NH Ar7 R11-15 1524 CH3 NH Ar8 R11-19 1486 CH3 NH Ar7 R11-16 1525 CH3 NH Ar8 R11-20 1487 CH3 NH Ar7 R11-17 1526 CH3 NH Ar8 R11-21 1488 CH3 NH Ar7 R11-18 1527 CH3 NH Ar8 R11-22 1489 CH3 NH Ar7 R11-19 1528 CH3 NH Ar8 R11-23 1490 CH3 NH Ar7 R11-20 1529 CH3 NH Ar8 R11-24 1491 CH3 NH Ar7 R11-21 1530 CH3 NH Ar8 R11-25 1492 CH3 NH Ar7 R11-22 1531 CH3 NH Ar8 R11-26 1493 CH3 NH Ar7 R11-23 1532 CH3 NH Ar8 R11-27 1494 CH3 NH Ar7 R11-24 1533 CH3 NH Ar8 R11-28 1495 CH3 NH Ar7 R11-25 1534 CH3 NH Ar8 R11-29 1496 CH3 NH Ar7 R11-26 1535 CH3 NH Ar8 A11-la 1497 CH3 NH Ar7 R11-27 1536 CH3 NH Ar8 A11-lb 1498 CH3 NH Ar7 R11-28 1537 CH3 NH Ar8 A11-2a 1499 CH3 NH Ar7 R11-29 1538 CH3 NH Ar8 A11-2b 1500 CH3 NH Ar7 A11-la 1539 CH3 NH Ar8 A11-3a 1501 CH3 NH AC A11-lb 1540 CH3 NH Ar8 A11-3b 1502 CH3 NH Ar7 A11-2a 1541 CH3 NH Ar9 R11-1 1503 CH3 NH Ar7 A11-2b 1542 CH3 NH Ar9 R11-2 1504 CH3 NH AC A11-3a 1543 CH3 NH Ar9 R11-3 1505 CH3 NH AC A11-3b 1544 CH3 NH Ar9 R11-4 1506 CH3 NH Ar8 R11-1 1545 CH3 NH Ar9 R11-5 1507 CH3 NH Ar8 R11-2 1546 CH3 NH Ar9 R11-6 1508 CH3 NH Ar8 R11-3 1547 CH3 NH Ar9 R11-7 1509 CH3 NH Ar8 R11-4 1548 CH3 NH Ar9 R11-8 1510 CH3 NH Ar8 R11-5 1549 CH3 NH Ar9 R11-9 1511 CH3 NH Ar8 R11-6 1550 CH3 NH Ar9 R11-10 1512 CH3 NH Ar8 R11-7 1551 CH3 NH Ar9 R11-11 1513 CH3 NH Ar8 R11-8 1552 CH3 NH Ar9 R11-12 Line R Q Ar D Line R Q Ar D
1553 CH3 NH Ar9 R11-13 1592 CH3 NH Arl R11-17 1554 CH3 NH Ar9 R11-14 1593 CH3 NH Arl R11-18 1555 CH3 NH Ar9 R11-15 1594 CH3 NH Arlo R11-19 1556 CH3 NH Ar9 R11-16 1595 CH3 NH Arlo R11-20 1557 CH3 NH Ar9 R11-17 1596 CH3 NH Arl R11-21 1558 CH3 NH Ar9 R11-18 1597 CH3 NH Arlo R11-22 1559 CH3 NH Ar9 R11-19 1598 CH3 NH Arlo R11-23 1560 CH3 NH Ar9 R11-20 1599 CH3 NH Arlo R11-24 1561 CH3 NH Ar9 R11-21 1600 CH3 NH Arlo R11-25 1562 CH3 NH Ar9 R11-22 1601 CH3 NH Arlo R11-26 1563 CH3 NH Ar9 R11-23 1602 CH3 NH Arlo R11-27 1564 CH3 NH Ar9 R11-24 1603 CH3 NH Arlo R11-28 1565 CH3 NH Ar9 R11-25 1604 CH3 NH Arlo R11-29 1566 CH3 NH Ar9 R11-26 1605 CH3 NH Arlo A11-la 1567 CH3 NH Ar9 R11-27 1606 CH3 NH Arlo A11-lb 1568 CH3 NH Ar9 R11-28 1607 CH3 NH Arlo A11-2a 1569 CH3 NH Ar9 R11-29 1608 CH3 NH Arlo A11-2b 1570 CH3 NH Ar9 A11-la 1609 CH3 NH Arlo A11-3a 1571 CH3 NH Ar9 A11-lb 1610 CH3 NH Arlo A11-3b 1572 CH3 NH Ar9 A11-2a 1611 CH3 NH Aril R11-1 1573 CH3 NH Ar9 A11-2b 1612 CH3 NH Aril R11-2 1574 CH3 NH Ar9 A11-3a 1613 CH3 NH Aril R11-3 1575 CH3 NH Ar9 A11-3b 1614 CH3 NH Aril R11-4 1576 CH3 NH Arlo R11-1 1615 CH3 NH Aril R11-5 1577 CH3 NH Arlo R11-2 1616 CH3 NH Aril R11-6 1578 CH3 NH Arlo R11-3 1617 CH3 NH Aril R11-7 1579 CH3 NH Arl R11-4 1618 CH3 NH Aril R11-8 1580 CH3 NH Arlo R11-5 1619 CH3 NH Aril R11-9 1581 CH3 NH Arlo R11-6 1620 CH3 NH Aril R11-10 1582 CH3 NH Arl R11-7 1621 CH3 NH Aril R11-11 1583 CH3 NH Arl R11-8 1622 CH3 NH Aril R11-12 1584 CH3 NH Arl R11-9 1623 CH3 NH Aril R11-13 1585 CH3 NH Arlo R11-10 1624 CH3 NH Aril R11-14 1586 CH3 NH Arl R11-11 1625 CH3 NH Aril R11-15 1587 CH3 NH Arl R11-12 1626 CH3 NH Aril R11-16 1588 CH3 NH Arlo R11-13 1627 CH3 NH Aril R11-17 1589 CH3 NH Arlo R11-14 1628 CH3 NH Aril R11-18 1590 CH3 NH Arlo R11-15 1629 CH3 NH Aril R11-19 1591 CH3 NH Arlo R11-16 1630 CH3 NH Aril R11-20 Line R Q Ar D Line R Q Ar D
1631 CH3 NH Aril R11-21 1670 CH3 NH Ar12 R11-25 1632 CH3 NH Aril R11-22 1671 CH3 NH Ar12 R11-26 1633 CH3 NH Aril R11-23 1672 CH3 NH Ar12 R11-27 1634 CH3 NH Aril R11-24 1673 CH3 NH Ar12 R11-28 1635 CH3 NH Aril R11-25 1674 CH3 NH Ar12 R11-29 1636 CH3 NH Aril R11-26 1675 CH3 NH Ar12 A11-la 1637 CH3 NH Aril R11-27 1676 CH3 NH Ar12 A11-lb 1638 CH3 NH Aril R11-28 1677 CH3 NH Ar12 A11-2a 1639 CH3 NH Aril R11-29 1678 CH3 NH Ar12 A11-2b 1640 CH3 NH Aril A11-la 1679 CH3 NH Ar12 A11-3a 1641 CH3 NH Aril A11-lb 1680 CH3 NH Ar12 A11-3b 1642 CH3 NH Aril A11-2a 1681 CH3 NCH3 Arl R11-1 1643 CH3 NH Aril A11-2b 1682 CH3 NCH3 Arl R11-2 1644 CH3 NH Aril A11-3a 1683 CH3 NCH3 Arl R11-3 1645 CH3 NH Aril A11-3b 1684 CH3 NCH3 Arl R11-4 1646 CH3 NH Ar12 R11-1 1685 CH3 NCH3 Arl R11-5 1647 CH3 NH Ar12 R11-2 1686 CH3 NCH3 Arl R11-6 1648 CH3 NH Ar12 R11-3 1687 CH3 NCH3 Arl R11-7 1649 CH3 NH Ar12 R11-4 1688 CH3 NCH3 Arl R11-8 1650 CH3 NH Ar12 R11-5 1689 CH3 NCH3 Arl R11-9 1651 CH3 NH Ar12 R11-6 1690 CH3 NCH3 Arl R11-10 1652 CH3 NH Ar12 R11-7 1691 CH3 NCH3 Arl R11-11 1653 CH3 NH Ar12 R11-8 1692 CH3 NCH3 Arl R11-12 1654 CH3 NH Ar12 R11-9 1693 CH3 NCH3 Arl R11-13 1655 CH3 NH Ar12 R11-10 1694 CH3 NCH3 Arl R11-14 1656 CH3 NH Ar12 R11-11 1695 CH3 NCH3 Arl R11-15 1657 CH3 NH Ar12 R11-12 1696 CH3 NCH3 Arl R11-16 1658 CH3 NH Ar12 R11-13 1697 CH3 NCH3 Arl R11-17 1659 CH3 NH Ar12 R11-14 1698 CH3 NCH3 Arl R11-18 1660 CH3 NH Ar12 R11-15 1699 CH3 NCH3 Arl R11-19 1661 CH3 NH Ar12 R11-16 1700 CH3 NCH3 Arl R11-20 1662 CH3 NH Ar12 R11-17 1701 CH3 NCH3 Arl R11-21 1663 CH3 NH Ar12 R11-18 1702 CH3 NCH3 Arl R11-22 1664 CH3 NH Ar12 R11-19 1703 CH3 NCH3 Arl R11-23 1665 CH3 NH Ar12 R11-20 1704 CH3 NCH3 Arl R11-24 1666 CH3 NH Ar12 R11-21 1705 CH3 NCH3 Arl R11-25 1667 CH3 NH Ar12 R11-22 1706 CH3 NCH3 Arl R11-26 1668 CH3 NH Ar12 R11-23 1707 CH3 NCH3 Arl R11-27 1669 CH3 NH Ar12 R11-24 1708 CH3 NCH3 Arl R11-28 Line R Q Ar D Line R Q Ar D
1709 CH3 NCH3 Arl R11-29 1748 CH3 NCH3 Ar2 A11-2b 1710 CH3 NCH3 Arl A11-la 1749 CH3 NCH3 Ar2 A11-3a 1711 CH3 NCH3 Arl A11-lb 1750 CH3 NCH3 Ar2 A11-3b 1712 CH3 NCH3 Arl A11-2a 1751 CH3 NCH3 Ar3 R11-1 1713 CH3 NCH3 Arl A11-2b 1752 CH3 NCH3 Ar3 R11-2 1714 CH3 NCH3 Arl A11-3a 1753 CH3 NCH3 Ar3 R11-3 1715 CH3 NCH3 Arl A11-3b 1754 CH3 NCH3 Ar3 R11-4 1716 CH3 NCH3 Ar2 R11-1 1755 CH3 NCH3 Ar3 R11-5 1717 CH3 NCH3 Ar2 R11-2 1756 CH3 NCH3 Ar3 R11-6 1718 CH3 NCH3 Ar2 R11-3 1757 CH3 NCH3 Ar3 R11-7 1719 CH3 NCH3 Ar2 R11-4 1758 CH3 NCH3 Ar3 R11-8 1720 CH3 NCH3 Ar2 R11-5 1759 CH3 NCH3 Ar3 R11-9 1721 CH3 NCH3 Ar2 R11-6 1760 CH3 NCH3 Ar3 R11-10 1722 CH3 NCH3 Ar2 R11-7 1761 CH3 NCH3 Ar3 R11-11 1723 CH3 NCH3 Ar2 R11-8 1762 CH3 NCH3 Ar3 R11-12 1724 CH3 NCH3 Ar2 R11-9 1763 CH3 NCH3 Ar3 R11-13 1725 CH3 NCH3 Ar2 R11-10 1764 CH3 NCH3 Ar3 R11-14 1726 CH3 NCH3 Ar2 R11-11 1765 CH3 NCH3 Ar3 R11-15 1727 CH3 NCH3 Ar2 R11-12 1766 CH3 NCH3 Ar3 R11-16 1728 CH3 NCH3 Ar2 R11-13 1767 CH3 NCH3 Ar3 R11-17 1729 CH3 NCH3 Ar2 R11-14 1768 CH3 NCH3 Ar3 R11-18 1730 CH3 NCH3 Ar2 R11-15 1769 CH3 NCH3 Ar3 R11-19 1731 CH3 NCH3 Ar2 R11-16 1770 CH3 NCH3 Ar3 R11-20 1732 CH3 NCH3 Ar2 R11-17 1771 CH3 NCH3 Ar3 R11-21 1733 CH3 NCH3 Ar2 R11-18 1772 CH3 NCH3 Ar3 R11-22 1734 CH3 NCH3 Ar2 R11-19 1773 CH3 NCH3 Ar3 R11-23 1735 CH3 NCH3 Ar2 R11-20 1774 CH3 NCH3 Ar3 R11-24 1736 CH3 NCH3 Ar2 R11-21 1775 CH3 NCH3 Ar3 R11-25 1737 CH3 NCH3 Ar2 R11-22 1776 CH3 NCH3 Ar3 R11-26 1738 CH3 NCH3 Ar2 R11-23 1777 CH3 NCH3 Ar3 R11-27 1739 CH3 NCH3 Ar2 R11-24 1778 CH3 NCH3 Ar3 R11-28 1740 CH3 NCH3 Ar2 R11-25 1779 CH3 NCH3 Ar3 R11-29 1741 CH3 NCH3 Ar2 R11-26 1780 CH3 NCH3 Ar3 A11-la 1742 CH3 NCH3 Ar2 R11-27 1781 CH3 NCH3 Ar3 A11-lb 1743 CH3 NCH3 Ar2 R11-28 1782 CH3 NCH3 Ar3 A11-2a 1744 CH3 NCH3 Ar2 R11-29 1783 CH3 NCH3 Ar3 A11-2b 1745 CH3 NCH3 Ar2 A11-la 1784 CH3 NCH3 Ar3 A11-3a 1746 CH3 NCH3 Ar2 A11-lb 1785 CH3 NCH3 Ar4 A11-3b 1747 CH3 NCH3 Ar2 A11-2a 1786 CH3 NCH3 Ar4 R11-1 Line R Q Ar D Line R Q Ar D
1787 CH3 NCH3 AO R11-2 1826 CH3 NCH3 Ar5 R11-6 1788 CH3 NCH3 AO R11-3 1827 CH3 NCH3 Ar5 R11-7 1789 CH3 NCH3 Art R11-4 1828 CH3 NCH3 Ar5 R11-8 1790 CH3 NCH3 Art R11-5 1829 CH3 NCH3 Ar5 R11-9 1791 CH3 NCH3 AO R11-6 1830 CH3 NCH3 Ar5 R11-10 1792 CH3 NCH3 Art R11-7 1831 CH3 NCH3 Ar5 R11-11 1793 CH3 NCH3 Art R11-8 1832 CH3 NCH3 Ar5 R11-12 1794 CH3 NCH3 Art R11-9 1833 CH3 NCH3 Ar5 R11-13 1795 CH3 NCH3 Art R11-10 1834 CH3 NCH3 Ar5 R11-14 1796 CH3 NCH3 Art R11-11 1835 CH3 NCH3 Ar5 R11-15 1797 CH3 NCH3 Art R11-12 1836 CH3 NCH3 Ar5 R11-16 1798 CH3 NCH3 Art R11-13 1837 CH3 NCH3 Ar5 R11-17 1799 CH3 NCH3 Art R11-14 1838 CH3 NCH3 Ar5 R11-18 1800 CH3 NCH3 Art R11-15 1839 CH3 NCH3 Ar5 R11-19 1801 CH3 NCH3 Art R11-16 1840 CH3 NCH3 Ar5 R11-20 1802 CH3 NCH3 Art R11-17 1841 CH3 NCH3 Ar5 R11-21 1803 CH3 NCH3 Art R11-18 1842 CH3 NCH3 Ar5 R11-22 1804 CH3 NCH3 Art R11-19 1843 CH3 NCH3 Ar5 R11-23 1805 CH3 NCH3 Art R11-20 1844 CH3 NCH3 Ar5 R11-24 1806 CH3 NCH3 Art R11-21 1845 CH3 NCH3 Ar5 R11-25 1807 CH3 NCH3 Art R11-22 1846 CH3 NCH3 Ar5 R11-26 1808 CH3 NCH3 Art R11-23 1847 CH3 NCH3 Ar5 R11-27 1809 CH3 NCH3 Art R11-24 1848 CH3 NCH3 Ar5 R11-28 1810 CH3 NCH3 Art R11-25 1849 CH3 NCH3 Ar5 R11-29 1811 CH3 NCH3 Art R11-26 1850 CH3 NCH3 Ar5 A11-la 1812 CH3 NCH3 Art R11-27 1851 CH3 NCH3 Ar5 A11-lb 1813 CH3 NCH3 AO R11-28 1852 CH3 NCH3 Ar5 A11-2a 1814 CH3 NCH3 Art R11-29 1853 CH3 NCH3 Ar5 A11-2b 1815 CH3 NCH3 Art A11-la 1854 CH3 NCH3 Ar5 A11-3a 1816 CH3 NCH3 AO A11-lb 1855 CH3 NCH3 Ar5 A11-3b 1817 CH3 NCH3 AO A11-2a 1856 CH3 NCH3 Ar6 R11-1 1818 CH3 NCH3 AO A11-2b 1857 CH3 NCH3 Ar6 R11-2 1819 CH3 NCH3 Art A11-3a 1858 CH3 NCH3 Ar6 R11-3 1820 CH3 NCH3 AO A11-3b 1859 CH3 NCH3 Ar6 R11-4 1821 CH3 NCH3 Ar5 R11-1 1860 CH3 NCH3 Ar6 R11-5 1822 CH3 NCH3 Ar5 R11-2 1861 CH3 NCH3 Ar6 R11-6 1823 CH3 NCH3 Ar5 R11-3 1862 CH3 NCH3 Ar6 R11-7 1824 CH3 NCH3 Ar5 R11-4 1863 CH3 NCH3 Ar6 R11-8 1825 CH3 NCH3 Ar5 R11-5 1864 CH3 NCH3 Ar6 R11-9 Line R Q Ar D Line R Q Ar D
1865 CH3 NCH3 Ar6 R11-10 1904 CH3 NCH3 Ar7 R11-14 1866 CH3 NCH3 Ar6 R11-11 1905 CH3 NCH3 Ar7 R11-15 1867 CH3 NCH3 Ar6 R11-12 1906 CH3 NCH3 Ar7 R11-16 1868 CH3 NCH3 Ar6 R11-13 1907 CH3 NCH3 Ar7 R11-17 1869 CH3 NCH3 Ar6 R11-14 1908 CH3 NCH3 Ar7 R11-18 1870 CH3 NCH3 Ar6 R11-15 1909 CH3 NCH3 Ar7 R11- 1 9 1871 CH3 NCH3 Ar6 R11-16 1910 CH3 NCH3 Ar7 R11-20 1872 CH3 NCH3 Ar6 R11-17 1911 CH3 NCH3 Ar7 R11-21 1873 CH3 NCH3 Ar6 R11-18 1912 CH3 NCH3 Ar7 R11-22 1874 CH3 NCH3 Ar6 R11-19 1913 CH3 NCH3 Ar7 R11-23 1875 CH3 NCH3 Ar6 R11-20 1914 CH3 NCH3 Ar7 R11-24 1876 CH3 NCH3 Ar6 R11-21 1915 CH3 NCH3 Ar7 R11-25 1877 CH3 NCH3 Ar6 R11-22 1916 CH3 NCH3 Ar7 R11-26 1878 CH3 NCH3 Ar6 R11-23 1917 CH3 NCH3 Ar7 R11-27 1879 CH3 NCH3 Ar6 R11-24 1918 CH3 NCH3 Ar7 R11-28 1880 CH3 NCH3 Ar6 R11-25 1919 CH3 NCH3 Ar7 R11-29 1881 CH3 NCH3 Ar6 R11-26 1920 CH3 NCH3 Ar7 A11-la 1882 CH3 NCH3 Ar6 R11-27 1921 CH3 NCH3 Ar7 A11-lb 1883 CH3 NCH3 Ar6 R11-28 1922 CH3 NCH3 Ar7 A11-2a 1884 CH3 NCH3 Ar6 R11-29 1923 CH3 NCH3 Ar7 A11-2b 1885 CH3 NCH3 Ar6 A11-la 1924 CH3 NCH3 Ar7 A11-3a 1886 CH3 NCH3 Ar6 A11-lb 1925 CH3 NCH3 Ar7 A11-3b 1887 CH3 NCH3 Ar6 A11-2a 1926 CH3 NCH3 Ar8 R11-1 1888 CH3 NCH3 Ar6 A11-2b 1927 CH3 NCH3 Ar8 R11-2 1889 CH3 NCH3 Ar6 A11-3a 1928 CH3 NCH3 Ar8 R11-3 1890 CH3 NCH3 Ar6 A11-3b 1929 CH3 NCH3 Ar8 R11-4 1891 CH3 NCH3 Ar7 R11-1 1930 CH3 NCH3 AO R11-5 1892 CH3 NCH3 Ar7 R11-2 1931 CH3 NCH3 Ar8 R11-6 1893 CH3 NCH3 Ar7 R11-3 1932 CH3 NCH3 Ar8 R11-7 1894 CH3 NCH3 Ar7 R11-4 1933 CH3 NCH3 AO R11-8 1895 CH3 NCH3 Ar7 R11-5 1934 CH3 NCH3 AO R11-9 1896 CH3 NCH3 Ar7 R11-6 1935 CH3 NCH3 AO R11- 1 0 1897 CH3 NCH3 Ar7 R11-7 1936 CH3 NCH3 Ar8 R11-11 1898 CH3 NCH3 Ar7 R11-8 1937 CH3 NCH3 AO R11-12 1899 CH3 NCH3 Ar7 R11-9 1938 CH3 NCH3 AO R11- 1 3 1900 CH3 NCH3 Ar7 R11-10 1939 CH3 NCH3 Ar8 R11-14 1901 CH3 NCH3 Ar7 R11-11 1940 CH3 NCH3 Ar8 R11- 1 5 1902 CH3 NCH3 Ar7 R11- 1 2 1941 CH3 NCH3 Ar8 R11- 1 6 1903 CH3 NCH3 Ar7 R11-13 1942 CH3 NCH3 Ar8 R11- 1 7 Line R Q Ar D Line R Q Ar D
1943 CH3 NCH3 Ar8 R11-18 1982 CH3 NCH3 Ar9 R11-22 1944 CH3 NCH3 Ar8 R11-19 1983 CH3 NCH3 Ar9 R11-23 1945 CH3 NCH3 Ar8 R11-20 1984 CH3 NCH3 Ar9 R11-24 1946 CH3 NCH3 Ar8 R11-21 1985 CH3 NCH3 Ar9 R11-25 1947 CH3 NCH3 Ar8 R11-22 1986 CH3 NCH3 Ar9 R11-26 1948 CH3 NCH3 Ar8 R11-23 1987 CH3 NCH3 Ar9 R11-27 1949 CH3 NCH3 Ar8 R11-24 1988 CH3 NCH3 Ar9 R11-28 1950 CH3 NCH3 Ar8 R11-25 1989 CH3 NCH3 Ar9 R11-29 1951 CH3 NCH3 Ar8 R11-26 1990 CH3 NCH3 Ar9 A11-la 1952 CH3 NCH3 Ar8 R11-27 1991 CH3 NCH3 Ar9 A11-lb 1953 CH3 NCH3 Ar8 R11-28 1992 CH3 NCH3 Ar9 A11-2a 1954 CH3 NCH3 Ar8 R11-29 1993 CH3 NCH3 Ar9 A11-2b 1955 CH3 NCH3 Ar8 A11-la 1994 CH3 NCH3 Ar9 A11-3a 1956 CH3 NCH3 Ar8 A11-lb 1995 CH3 NCH3 Ar9 A11-3b 1957 CH3 NCH3 Ar8 A11-2a 1996 CH3 NCH3 Arlo R11-1 1958 CH3 NCH3 Ar8 A11-2b 1997 CH3 NCH3 Arlo R11-2 1959 CH3 NCH3 Ar8 A11-3a 1998 CH3 NCH3 Arlo R11-3 1960 CH3 NCH3 Ar8 A11-3b 1999 CH3 NCH3 Arlo R11-4 1961 CH3 NCH3 Ar9 R11-1 2000 CH3 NCH3 Arlo R11-5 1962 CH3 NCH3 Ar9 R11-2 2001 CH3 NCH3 Arlo R11-6 1963 CH3 NCH3 Ar9 R11-3 2002 CH3 NCH3 Arlo R11-7 1964 CH3 NCH3 Ar9 R11-4 2003 CH3 NCH3 Arlo R11-8 1965 CH3 NCH3 Ar9 R11-5 2004 CH3 NCH3 Arlo R11-9 1966 CH3 NCH3 Ar9 R11-6 2005 CH3 NCH3 Arlo R11-10 1967 CH3 NCH3 Ar9 R11-7 2006 CH3 NCH3 Arlo R11-11 1968 CH3 NCH3 Ar9 R11-8 2007 CH3 NCH3 Arlo R11-12 1969 CH3 NCH3 Ar9 R11-9 2008 CH3 NCH3 Arl R11-13 1970 CH3 NCH3 Ar9 R11-10 2009 CH3 NCH3 Arlo R11-14 1971 CH3 NCH3 Ar9 R11-11 2010 CH3 NCH3 Arlo R11-15 1972 CH3 NCH3 Ar9 R11-12 2011 CH3 NCH3 Arl R11-16 1973 CH3 NCH3 Ar9 R11-13 2012 CH3 NCH3 Arl R11-17 1974 CH3 NCH3 Ar9 R11-14 2013 CH3 NCH3 Arl R11-18 1975 CH3 NCH3 Ar9 R11-15 2014 CH3 NCH3 Arlo R11-19 1976 CH3 NCH3 Ar9 R11-16 2015 CH3 NCH3 Arl R11-20 1977 CH3 NCH3 Ar9 R11-17 2016 CH3 NCH3 Arl R11-21 1978 CH3 NCH3 Ar9 R11-18 2017 CH3 NCH3 Arlo R11-22 1979 CH3 NCH3 Ar9 R11-19 2018 CH3 NCH3 Arlo R11-23 1980 CH3 NCH3 Ar9 R11-20 2019 CH3 NCH3 Arlo R11-24 1981 CH3 NCH3 Ar9 R11-21 2020 CH3 NCH3 Arlo R11-25 Line R Q Ar D Line R Q Ar D
2021 CH3 NCH3 Arl R11-26 2060 CH3 NCH3 Aril A11-la 2022 CH3 NCH3 Arl R11-27 2061 CH3 NCH3 Aril A11-lb 2023 CH3 NCH3 Arlo R11-28 2062 CH3 NCH3 Aril A11-2a 2024 CH3 NCH3 Arlo R11-29 2063 CH3 NCH3 Aril A11-2b 2025 CH3 NCH3 Arl A11-la 2064 CH3 NCH3 Aril A11-3a 2026 CH3 NCH3 Arlo A11-lb 2065 CH3 NCH3 Aril A11-3b 2027 CH3 NCH3 Arlo A11-2a 2066 CH3 NCH3 Ar12 R11-1 2028 CH3 NCH3 Arlo A11-2b 2067 CH3 NCH3 Ar12 R11-2 2029 CH3 NCH3 Arlo A11-3a 2068 CH3 NCH3 Ar12 R11-3 2030 CH3 NCH3 Arlo A11-3b 2069 CH3 NCH3 Ar12 R11-4 2031 CH3 NCH3 Aril R11-1 2070 CH3 NCH3 Ar12 R11-5 2032 CH3 NCH3 Aril R11-2 2071 CH3 NCH3 Ar12 R11-6 2033 CH3 NCH3 Aril R11-3 2072 CH3 NCH3 Ar12 R11-7 2034 CH3 NCH3 Aril R11-4 2073 CH3 NCH3 Ar12 R11-8 2035 CH3 NCH3 Aril R11-5 2074 CH3 NCH3 Ar12 R11-9 2036 CH3 NCH3 Aril R11-6 2075 CH3 NCH3 Ar12 R11-10 2037 CH3 NCH3 Aril R11-7 2076 CH3 NCH3 Ar12 R11-11 2038 CH3 NCH3 Aril R11-8 2077 CH3 NCH3 Ar12 R11-12 2039 CH3 NCH3 Aril R11-9 2078 CH3 NCH3 Ar12 R11-13 2040 CH3 NCH3 Aril R11-10 2079 CH3 NCH3 Ar12 R11-14 2041 CH3 NCH3 Aril R11-11 2080 CH3 NCH3 Ar12 R11-15 2042 CH3 NCH3 Aril R11-12 2081 CH3 NCH3 Ar12 R11-16 2043 CH3 NCH3 Aril R11-13 2082 CH3 NCH3 Ar12 R11-17 2044 CH3 NCH3 Aril R11-14 2083 CH3 NCH3 Ar12 R11-18 2045 CH3 NCH3 Aril R11-15 2084 CH3 NCH3 Ar12 R11-19 2046 CH3 NCH3 Aril R11-16 2085 CH3 NCH3 Ar12 R11-20 2047 CH3 NCH3 Aril R11-17 2086 CH3 NCH3 Ar12 R11-21 2048 CH3 NCH3 Aril R11-18 2087 CH3 NCH3 Ar12 R11-22 2049 CH3 NCH3 Aril R11-19 2088 CH3 NCH3 Ar12 R11-23 2050 CH3 NCH3 Aril R11-20 2089 CH3 NCH3 Ar12 R11-24 2051 CH3 NCH3 Aril R11-21 2090 CH3 NCH3 Ar12 R11-25 2052 CH3 NCH3 Aril R11-22 2091 CH3 NCH3 Ar12 R11-26 2053 CH3 NCH3 Aril R11-23 2092 CH3 NCH3 Ar12 R11-27 2054 CH3 NCH3 Aril R11-24 2093 CH3 NCH3 Ar12 R11-28 2055 CH3 NCH3 Aril R11-25 2094 CH3 NCH3 Ar12 R11-29 2056 CH3 NCH3 Aril R11-26 2095 CH3 NCH3 Ar12 A11-la 2057 CH3 NCH3 Aril R11-27 2096 CH3 NCH3 Ar12 A11-lb 2058 CH3 NCH3 Aril R11-28 2097 CH3 NCH3 Ar12 A11-2a 2059 CH3 NCH3 Aril R11-29 2098 CH3 NCH3 Ar12 A11-2b Line R Q Ar D Line R Q Ar D
2099 CH3 NCH3 Ar12 A11-3a 2138 CH3 0 Ar2 R11-3 2100 CH3 NCH3 Ar12 A11-3b 2139 CH3 0 Ar2 R11-4 2101 CH3 0 Arl R11-1 2140 CH3 0 Ar2 R11-5 2102 CH3 0 Arl R11-2 2141 CH3 0 Ar2 R11-6 2103 CH3 0 Arl R11-3 2142 CH3 0 Ar2 R11-7 2104 CH3 0 Arl R11-4 2143 CH3 0 Ar2 R11-8 2105 CH3 0 Arl R11-5 2144 CH3 0 Ar2 R11-9 2106 CH3 0 Arl R11-6 2145 CH3 0 Ar2 R11-10 2107 CH3 0 Arl R11-7 2146 CH3 0 Ar2 R11-11 2108 CH3 0 Arl R11-8 2147 CH3 0 Ar2 R11-12 2109 CH3 0 Arl R11-9 2148 CH3 0 Ar2 R11-13 2110 CH3 0 Arl R11-10 2149 CH3 0 Ar2 R11-14 2111 CH3 0 Arl R11-11 2150 CH3 0 Ar2 R11-15 2112 CH3 0 Arl R11-12 2151 CH3 0 Ar2 R11-16 2113 CH3 0 Arl R11-13 2152 CH3 0 Ar2 R11-17 2114 CH3 0 Arl R11-14 2153 CH3 0 Ar2 R11-18 2115 CH3 0 Arl R11-15 2154 CH3 0 Ar2 R11-19 2116 CH3 0 Arl R11-16 2155 CH3 0 Ar2 R11-20 2117 CH3 0 Arl R11-17 2156 CH3 0 Ar2 R11-21 2118 CH3 0 Arl R11-18 2157 CH3 0 Ar2 R11-22 2119 CH3 0 Arl R11-19 2158 CH3 0 Ar2 R11-23 2120 CH3 0 Arl R11-20 2159 CH3 0 Ar2 R11-24 2121 CH3 0 Arl R11-21 2160 CH3 0 Ar2 R11-25 2122 CH3 0 Arl R11-22 2161 CH3 0 Ar2 R11-26 2123 CH3 0 Arl R11-23 2162 CH3 0 Ar2 R11-27 2124 CH3 0 Arl R11-24 2163 CH3 0 Ar2 R11-28 2125 CH3 0 Arl R11-25 2164 CH3 0 Ar2 R11-29 2126 CH3 0 Arl R11-26 2165 CH3 0 Ar2 A11-la 2127 CH3 0 Arl R11-27 2166 CH3 0 Ar2 A11-lb 2128 CH3 0 Arl R11-28 2167 CH3 0 Ar2 A11-2a 2129 CH3 0 Arl R11-29 2168 CH3 0 Ar2 A11-2b 2130 CH3 0 Arl A11-la 2169 CH3 0 Ar2 A11-3a 2131 CH3 0 Arl A11-lb 2170 CH3 0 Ar2 A11-3b 2132 CH3 0 Arl A11-2a 2171 CH3 0 Ar3 R11-1 2133 CH3 0 Arl A11-2b 2172 CH3 0 Ar3 R11-2 2134 CH3 0 Arl A11-3a 2173 CH3 0 Ar3 R11-3 2135 CH3 0 Arl A11-3b 2174 CH3 0 Ar3 R11-4 2136 CH3 0 Ar2 R11-1 2175 CH3 0 Ar3 R11-5 2137 CH3 0 Ar2 R11-2 2176 CH3 0 Ar3 R11-6 Line R Q Ar D Line R Q Ar D
2177 CH3 0 Ar3 R11-7 2216 CH3 0 Ar4 R11-11 2178 CH3 0 Ar3 R11-8 2217 CH3 0 Ar4 R11-12 2179 CH3 0 Ar3 R11-9 2218 CH3 0 Ar4 R11-13 2180 CH3 0 Ar3 R11-10 2219 CH3 0 Ar4 R11-14 2181 CH3 0 Ar3 R11-11 2220 CH3 0 Ar4 R11-15 2182 CH3 0 Ar3 R11-12 2221 CH3 0 Ar4 R11-16 2183 CH3 0 Ar3 R11-13 2222 CH3 0 Ar4 R11-17 2184 CH3 0 Ar3 R11-14 2223 CH3 0 Ar4 R11-18 2185 CH3 0 Ar3 R11-15 2224 CH3 0 Ar4 R11-19 2186 CH3 0 Ar3 R11-16 2225 CH3 0 Ar4 R11-20 2187 CH3 0 Ar3 R11-17 2226 CH3 0 Ar4 R11-21 2188 CH3 0 Ar3 R11-18 2227 CH3 0 Ar4 R11-22 2189 CH3 0 Ar3 R11-19 2228 CH3 0 Ar4 R11-23 2190 CH3 0 Ar3 R11-20 2229 CH3 0 Ar4 R11-24 2191 CH3 0 Ar3 R11-21 2230 CH3 0 Ar4 R11-25 2192 CH3 0 Ar3 R11-22 2231 CH3 0 Ar4 R11-26 2193 CH3 0 Ar3 R11-23 2232 CH3 0 Ar4 R11-27 2194 CH3 0 Ar3 R11-24 2233 CH3 0 Ar4 R11-28 2195 CH3 0 Ar3 R11-25 2234 CH3 0 Ar4 R11-29 2196 CH3 0 Ar3 R11-26 2235 CH3 0 Ar4 A11-la 2197 CH3 0 Ar3 R11-27 2236 CH3 0 Ar4 A11-lb 2198 CH3 0 Ar3 R11-28 2237 CH3 0 Ar4 A11-2a 2199 CH3 0 Ar3 R11-29 2238 CH3 0 Ar4 A11-2b 2200 CH3 0 Ar3 A11-la 2239 CH3 0 Ar4 A11-3a 2201 CH3 0 Ar3 A11-lb 2240 CH3 0 Ar4 A11-3b 2202 CH3 0 Ar3 A11-2a 2241 CH3 0 Ar5 R11-1 2203 CH3 0 Ar3 A11-2b 2242 CH3 0 Ar5 R11-2 2204 CH3 0 Ar3 A11-3a 2243 CH3 0 Ar5 R11-3 2205 CH3 0 Ar4 A11-3b 2244 CH3 0 Ar5 R11-4 2206 CH3 0 AO R11-1 2245 CH3 0 Ar5 R11-5 2207 CH3 0 AO R11-2 2246 CH3 0 Ar5 R11-6 2208 CH3 0 AO R11-3 2247 CH3 0 Ar5 R11-7 2209 CH3 0 Art R11-4 2248 CH3 0 Ar5 R11-8 2210 CH3 0 AO R11-5 2249 CH3 0 Ar5 R11-9 2211 CH3 0 AO R11-6 2250 CH3 0 Ar5 R11-10 2212 CH3 0 Art R11-7 2251 CH3 0 Ar5 R11-11 2213 CH3 0 Art R11-8 2252 CH3 0 Ar5 R11-12 2214 CH3 0 Art R11-9 2253 CH3 0 Ar5 R11-13 2215 CH3 0 Art R11-10 2254 CH3 0 Ar5 R11-14 Line R Q Ar D Line R Q Ar D
2255 CH3 0 Ar5 R11-15 2294 CH3 0 Ar6 R11-19 2256 CH3 0 Ar5 R11-16 2295 CH3 0 Ar6 R11-20 2257 CH3 0 Ar5 R11-17 2296 CH3 0 Ar6 R11-21 2258 CH3 0 Ar5 R11-18 2297 CH3 0 Ar6 R11-22 2259 CH3 0 Ar5 R11-19 2298 CH3 0 Ar6 R11-23 2260 CH3 0 Ar5 R11-20 2299 CH3 0 Ar6 R11-24 2261 CH3 0 Ar5 R11-21 2300 CH3 0 Ar6 R11-25 2262 CH3 0 Ar5 R11-22 2301 CH3 0 Ar6 R11-26 2263 CH3 0 Ar5 R11-23 2302 CH3 0 Ar6 R11-27 2264 CH3 0 Ar5 R11-24 2303 CH3 0 Ar6 R11-28 2265 CH3 0 Ar5 R11-25 2304 CH3 0 Ar6 R11-29 2266 CH3 0 Ar5 R11-26 2305 CH3 0 Ar6 A11-la 2267 CH3 0 Ar5 R11-27 2306 CH3 0 Ar6 A11-lb 2268 CH3 0 Ar5 R11-28 2307 CH3 0 Ar6 A11-2a 2269 CH3 0 Ar5 R11-29 2308 CH3 0 Ar6 A11-2b 2270 CH3 0 Ar5 A11-la 2309 CH3 0 Ar6 A11-3a 2271 CH3 0 Ar5 A11-lb 2310 CH3 0 Ar6 A11-3b 2272 CH3 0 Ar5 A11-2a 2311 CH3 0 Ar7 R11-1 2273 CH3 0 Ar5 A11-2b 2312 CH3 0 Ar7 R11-2 2274 CH3 0 Ar5 A11-3a 2313 CH3 0 Ar7 R11-3 2275 CH3 0 Ar5 A11-3b 2314 CH3 0 Ar7 R11-4 2276 CH3 0 Ar6 R11-1 2315 CH3 0 Ar7 R11-5 2277 CH3 0 Ar6 R11-2 2316 CH3 0 Ar7 R11-6 2278 CH3 0 Ar6 R11-3 2317 CH3 0 Ar7 R11-7 2279 CH3 0 Ar6 R11-4 2318 CH3 0 Ar7 R11-8 2280 CH3 0 Ar6 R11-5 2319 CH3 0 Ar7 R11-9 2281 CH3 0 Ar6 R11-6 2320 CH3 0 Ar7 R11-10 2282 CH3 0 Ar6 R11-7 2321 CH3 0 Ar7 R11-11 2283 CH3 0 Ar6 R11-8 2322 CH3 0 Ar7 R11-12 2284 CH3 0 Ar6 R11-9 2323 CH3 0 Ar7 R11-13 2285 CH3 0 Ar6 R11-10 2324 CH3 0 Ar7 R11-14 2286 CH3 0 Ar6 R11-11 2325 CH3 0 Ar7 R11-15 2287 CH3 0 Ar6 R11-12 2326 CH3 0 Ar7 R11-16 2288 CH3 0 Ar6 R11-13 2327 CH3 0 Ar7 R11-17 2289 CH3 0 Ar6 R11-14 2328 CH3 0 Ar7 R11-18 2290 CH3 0 Ar6 R11-15 2329 CH3 0 Ar7 R11-19 2291 CH3 0 Ar6 R11-16 2330 CH3 0 Ar7 R11-20 2292 CH3 0 Ar6 R11-17 2331 CH3 0 Ar7 R11-21 2293 CH3 0 Ar6 R11-18 2332 CH3 0 Ar7 R11-22 Line R Q Ar D Line R Q Ar D
2335 CH3 0 Ar7 R11-25 2374 CH3 0 Ar8 R11-29 2336 CH3 0 Ar7 R11-26 2375 CH3 0 Ar8 A11-la 2337 CH3 0 AC R11-27 2376 CH3 0 AO A11-lb 2338 CH3 0 Ar7 R11-28 2377 CH3 0 Ar8 A11-2a 2339 CH3 0 Ar7 R11-29 2378 CH3 0 Ar8 A11-21D
2340 CH3 0 Ar7 A11-la 2379 CH3 0 Ar8 A11-3a 2341 CH3 0 Ar7 A11-lb 2380 CH3 0 Ar8 A11-31D
2342 CH3 0 Ar7 A11-2a 2381 CH3 0 Ar8 R11-1 2343 CH3 0 Ar7 A11-2b 2382 CH3 0 Ar8 R11-2 2344 CH3 0 Ar7 A11-3a 2383 CH3 0 Ar8 R11-3 2345 CH3 0 Ar7 A11-3b 2384 CH3 0 Ar9 R11-4 2346 CH3 0 Ar8 R11-1 2385 CH3 0 Ar9 R11-5 2347 CH3 0 Ar8 R11-2 2386 CH3 0 Ar9 R11-6 2348 CH3 0 Ar8 R11-3 2387 CH3 0 Ar9 R11-7 2349 CH3 0 Ar8 R11-4 2388 CH3 0 Ar9 R11-8 2350 CH3 0 Ar8 R11-5 2389 CH3 0 Ar9 R11-9 2351 CH3 0 Ar8 R11-6 2390 CH3 0 Ar9 R11-10 2352 CH3 0 Ar8 R11-7 2391 CH3 0 Ar9 R11-11 2353 CH3 0 Ar8 R11-8 2392 CH3 0 Ar9 R11-12 2354 CH3 0 Ar8 R11-9 2393 CH3 0 Ar9 R11-13 2355 CH3 0 Ar8 R11-10 2394 CH3 0 Ar9 R11-14 2356 CH3 0 Ar8 R11-11 2395 CH3 0 Ar9 R11-15 2357 CH3 0 Ar8 R11-12 2396 CH3 0 Ar9 R11-16 2358 CH3 0 Ar8 R11-13 2397 CH3 0 Ar9 R11-17 2359 CH3 0 Ar8 R11-14 2398 CH3 0 Ar9 R11-18 2360 CH3 0 Ar8 R11-15 2399 CH3 0 Ar9 R11-19 2361 CH3 0 Ar8 R11-16 2400 CH3 0 Ar9 R11-20 2362 CH3 0 Ar8 R11-17 2401 CH3 0 Ar9 R11-21 2363 CH3 0 Ar8 R11-18 2402 CH3 0 Ar9 R11-22 2364 CH3 0 Ar8 R11-19 2403 CH3 0 Ar9 R11-23 2365 CH3 0 Ar8 R11-20 2404 CH3 0 Ar9 R11-24 2366 CH3 0 Ar8 R11-21 2405 CH3 0 Ar9 R11-25 2367 CH3 0 Ar8 R11-22 2406 CH3 0 Ar9 R11-26 2368 CH3 0 Ar8 R11-23 2407 CH3 0 Ar9 R11-27 2369 CH3 0 Ar8 R11-24 2408 CH3 0 Ar9 R11-28 2370 CH3 0 Ar8 R11-25 2409 CH3 0 Ar9 R11-29 2371 CH3 0 Ar8 R11-26 2410 CH3 0 Ar9 A11-la Line R Q Ar D Line R Q Ar D
2411 CH3 0 Ar9 A11-lb 2450 CH3 0 Arl A11-3b 2412 CH3 0 Ar9 A11-2a 2451 CH3 0 Aril R11-1 2413 CH3 0 Ar9 A11-2b 2452 CH3 0 Aril R11-2 2414 CH3 0 Ar9 A11-3a 2453 CH3 0 Aril R11-3 2415 CH3 0 Ar9 A11-3b 2454 CH3 0 Aril R11-4 2416 CH3 0 Arlo R11-1 2455 CH3 0 Aril R11-5 2417 CH3 0 Arlo R11-2 2456 CH3 0 Aril R11-6 2418 CH3 0 Arlo R11-3 2457 CH3 0 Aril R11-7 2419 CH3 0 Arlo R11-4 2458 CH3 0 Aril R11-8 2420 CH3 0 Arlo R11-5 2459 CH3 0 Aril R11-9 2421 CH3 0 Arlo R11-6 2460 CH3 0 Aril R11-10 2422 CH3 0 Arlo R11-7 2461 CH3 0 Aril R11-11 2423 CH3 0 Arlo R11-8 2462 CH3 0 Aril R11-12 2424 CH3 0 Arlo R11-9 2463 CH3 0 Aril R11-13 2425 CH3 0 Arlo R11-10 2464 CH3 0 Aril R11-14 2426 CH3 0 Arlo R11-11 2465 CH3 0 Aril R11-15 2427 CH3 0 Arlo R11-12 2466 CH3 0 Aril R11-16 2428 CH3 0 Arlo R11-13 2467 CH3 0 Aril R11-17 2429 CH3 0 Arlo R11-14 2468 CH3 0 Aril R11-18 2430 CH3 0 Arlo R11-15 2469 CH3 0 Aril R11-19 2431 CH3 0 Arlo R11-16 2470 CH3 0 Aril R11-20 2432 CH3 0 Arlo R11-17 2471 CH3 0 Aril R11-21 2433 CH3 0 Arlo R11-18 2472 CH3 0 Aril R11-22 2434 CH3 0 Arlo R11-19 2473 CH3 0 Aril R11-23 2435 CH3 0 Arlo R11-20 2474 CH3 0 Aril R11-24 2436 CH3 0 Arlo R11-21 2475 CH3 0 Aril R11-25 2437 CH3 0 Arl R11-22 2476 CH3 0 Aril R11-26 2438 CH3 0 Arlo R11-23 2477 CH3 0 Aril R11-27 2439 CH3 0 Arlo R11-24 2478 CH3 0 Aril R11-28 2440 CH3 0 Arl R11-25 2479 CH3 0 Aril R11-29 2441 CH3 0 Arl R11-26 2480 CH3 0 Aril A11-la 2442 CH3 0 Arl R11-27 2481 CH3 0 Aril A11-lb 2443 CH3 0 Arlo R11-28 2482 CH3 0 Aril A11-2a 2444 CH3 0 Arl R11-29 2483 CH3 0 Aril A11-2b 2445 CH3 0 Arl A11-la 2484 CH3 0 Aril A11-3a 2446 CH3 0 Arlo A11-lb 2485 CH3 0 Aril A11-3b 2447 CH3 0 Arlo A11-2a 2486 CH3 0 Ar12 R11-1 2448 CH3 0 Arlo A11-2b 2487 CH3 0 Ar12 R11-2 2449 CH3 0 Arlo A11-3a 2488 CH3 0 Ar12 R11-3 Line R Q Ar D Line R Q Ar D
2489 CH3 0 Ar12 R11-4 2528 CI NH Arl R11-8 2490 CH3 0 Ar12 R11-5 2529 CI NH Arl R11-9 2491 CH3 0 Ar12 R11-6 2530 CI
NH Arl R11-10 2492 CH3 0 Ar12 R11-7 2531 CI
NH Arl R11-11 2493 CH3 0 Ar12 R11-8 2532 CI
NH Arl R11-12 2494 CH3 0 Ar12 R11-9 2533 CI
NH Arl R11-13 2495 CH3 0 Ar12 R11-10 2534 CI
NH Arl R11-14 2496 CH3 0 Ar12 R11-11 2535 CI
NH Arl R11-15 2497 CH3 0 Ar12 R11-12 2536 CI
NH Arl R11-16 2498 CH3 0 Ar12 R11-13 2537 CI
NH Arl R11-17 2499 CH3 0 Ar12 R11-14 2538 CI
NH Arl R11-18 2500 CH3 0 Ar12 R11-15 2539 CI
NH Arl R11-19 2501 CH3 0 Ar12 R11-16 2540 CI
NH Arl R11-20 2502 CH3 0 Ar12 R11-17 2541 CI
NH Arl R11-21 2503 CH3 0 Ar12 R11-18 2542 CI
NH Arl R11-22 2504 CH3 0 Ar12 R11-19 2543 CI
NH Arl R11-23 2505 CH3 0 Ar12 R11-20 2544 CI
NH Arl R11-24 2506 CH3 0 Ar12 R11-21 2545 CI
NH Arl R11-25 2507 CH3 0 Ar12 R11-22 2546 CI
NH Arl R11-26 2508 CH3 0 Ar12 R11-23 2547 CI
NH Arl R11-27 2509 CH3 0 Ar12 R11-24 2548 CI
NH Arl R11-28 2510 CH3 0 Ar12 R11-25 2549 CI
NH Arl R11-29 2511 CH3 0 Ar12 R11-26 2550 CI
NH Arl A11-la 2512 CH3 0 Ar12 R11-27 2551 CI
NH Arl A11-lb 2513 CH3 0 Ar12 R11-28 2552 CI
NH Arl A11-2a 2514 CH3 0 Ar12 R11-29 2553 CI
NH Arl A11-2b 2515 CH3 0 Ar12 A11-la 2554 CI NH Arl A11-3a 2516 CH3 0 Ar12 A11-lb 2555 CI NH Arl A11-3b 2517 CH3 0 Ar12 A11-2a 2556 CI NH Ar2 R11-1 2518 CH3 0 Ar12 A11-2b 2557 CI NH Ar2 R11-2 2519 CH3 0 Ar12 A11-3a 2558 CI NH Ar2 R11-3 2520 CH3 0 Ar12 A11-3b 2559 CI NH Ar2 R11-4 2521 CI NH Arl R11-1 2560 CI NH Ar2 R11-5 2522 CI NH Arl R11-2 2561 CI NH Ar2 R11-6 2523 CI NH Arl R11-3 2562 CI NH Ar2 R11-7 2524 CI NH Arl R11-4 2563 CI NH Ar2 R11-8 2525 CI NH Arl R11-5 2564 CI NH Ar2 R11-9 2526 CI NH Arl R11-6 2565 CI NH Ar2 R11-10 2527 CI NH Arl R11-7 2566 CI NH Ar2 R11-11 Line R Q Ar D Line R Q Ar D
2567 CI NH Ar2 R11-12 2606 CI NH Ar3 R11-16 2568 CI NH Ar2 R11-13 2607 Cl NH Ar3 R11-17 2569 CI NH Ar2 R11-14 2608 CI NH Ar3 R11-18 2570 CI NH Ar2 R11-15 2609 CI NH Ar3 R11-19 2571 CI NH Ar2 R11-16 2610 CI NH Ar3 R11-20 2572 CI NH Ar2 R11-17 2611 CI NH Ar3 R11-21 2573 CI NH Ar2 R11-18 2612 CI NH Ar3 R11-22 2574 CI NH Ar2 R11-19 2613 CI NH Ar3 R11-23 2575 CI NH Ar2 R11-20 2614 CI NH Ar3 R11-24 2576 CI NH Ar2 R11-21 2615 CI NH Ar3 R11-25 2577 CI NH Ar2 R11-22 2616 CI NH Ar3 R11-26 2578 CI NH Ar2 R11-23 2617 CI NH Ar3 R11-27 2579 CI NH Ar2 R11-24 2618 CI NH Ar3 R11-28 2580 CI NH Ar2 R11-25 2619 CI NH Ar3 R11-29 2581 CI NH Ar2 R11-26 2620 CI NH Ar3 A11-la 2582 CI NH Ar2 R11-27 2621 CI NH Ar3 A11-lb 2583 CI NH Ar2 R11-28 2622 CI NH Ar3 A11-2a 2584 CI NH Ar2 R11-29 2623 CI NH Ar3 A11-2b 2585 CI NH Ar2 A11-la 2624 CI NH Ar3 A11-3a 2586 CI NH Ar2 A11-lb 2625 CI NH Art A11-3b 2587 CI NH Ar2 A11-2a 2626 CI NH Art R11-1 2588 CI NH Ar2 A11-2b 2627 CI NH Art R11-2 2589 CI NH Ar2 A11-3a 2628 CI NH Art R11-3 2590 CI NH Ar2 A11-3b 2629 CI NH Art R11-4 2591 CI NH Ar3 R11-1 2630 CI NH Art R11-5 2592 CI NH Ar3 R11-2 2631 CI NH Art R11-6 2593 CI NH Ar3 R11-3 2632 CI NH AO R11-7 2594 CI NH Ar3 R11-4 2633 CI NH Art R11-8 2595 CI NH Ar3 R11-5 2634 CI NH Art R11-9 2596 CI NH Ar3 R11-6 2635 CI NH AO R11-10 2597 CI NH Ar3 R11-7 2636 CI NH AO R11-11 2598 CI NH Ar3 R11-8 2637 CI NH AO R11-12 2599 CI NH Ar3 R11-9 2638 CI NH Art R11-13 2600 CI NH Ar3 R11-10 2639 CI NH AO R11-14 2601 CI NH Ar3 R11-11 2640 CI NH AO R11-15 2602 CI NH Ar3 R11-12 2641 CI NH Art R11-16 2603 CI NH Ar3 R11-13 2642 CI NH Art R11-17 2604 CI NH Ar3 R11-14 2643 CI NH Art R11-18 2605 CI NH Ar3 R11-15 2644 CI NH Art R11-19 Line R Q Ar D Line R Q Ar D
2645 CI NH AO R11-20 2684 CI NH Ar5 R11-24 2646 CI NH AO R11-21 2685 Cl NH Ar5 R11-25 2647 CI NH Art R11-22 2686 CI NH Ar5 R11-26 2648 CI NH Art R11-23 2687 CI NH Ar5 R11-27 2649 CI NH AO R11-24 2688 CI NH Ar5 R11-28 2650 CI NH Art R11-25 2689 CI NH Ar5 R11-29 2651 CI NH Art R11-26 2690 CI NH Ar5 A11-la 2652 CI NH Art R11-27 2691 CI NH Ar5 A11-lb 2653 CI NH Art R11-28 2692 CI NH Ar5 A11-2a 2654 CI NH Art R11-29 2693 CI NH Ar5 A11-2b 2655 CI NH Art A11-la 2694 CI NH Ar5 A11-3a 2656 CI NH Art A11-1b 2695 CI NH Ar5 A11-3b 2657 CI NH Art A11-2a 2696 CI NH Ar6 R11-1 2658 CI NH Art A11-2b 2697 CI NH Ar6 R11-2 2659 CI NH Art A11-3a 2698 CI NH Ar6 R11-3 2660 CI NH Art A11-3b 2699 CI NH Ar6 R11-4 2661 CI NH Ar5 R11-1 2700 CI NH Ar6 R11-5 2662 CI NH Ar5 R11-2 2701 CI NH Ar6 R11-6 2663 CI NH Ar5 R11-3 2702 CI NH Ar6 R11-7 2664 CI NH Ar5 R11-4 2703 CI NH Ar6 R11-8 2665 CI NH Ar5 R11-5 2704 CI NH Ar6 R11-9 2666 CI NH Ar5 R11-6 2705 CI NH Ar6 R11-10 2667 CI NH Ar5 R11-7 2706 CI NH Ar6 R11-11 2668 CI NH Ar5 R11-8 2707 CI NH Ar6 R11-12 2669 CI NH Ar5 R11-9 2708 CI NH Ar6 R11-13 2670 CI NH Ar5 R11-10 2709 CI NH Ar6 R11-14 2671 CI NH Ar5 R11-11 2710 CI NH Ar6 R11-15 2672 CI NH Ar5 R11-12 2711 CI NH Ar6 R11-16 2673 CI NH Ar5 R11-13 2712 CI NH Ar6 R11-17 2674 CI NH Ar5 R11-14 2713 CI NH Ar6 R11-18 2675 CI NH Ar5 R11-15 2714 CI NH Ar6 R11-19 2676 CI NH Ar5 R11-16 2715 CI NH Ar6 R11-20 2677 CI NH Ar5 R11-17 2716 CI NH Ar6 R11-21 2678 CI NH Ar5 R11-18 2717 CI NH Ar6 R11-22 2679 CI NH Ar5 R11-19 2718 CI NH Ar6 R11-23 2680 CI NH Ar5 R11-20 2719 CI NH Ar6 R11-24 2681 CI NH Ar5 R11-21 2720 CI NH Ar6 R11-25 2682 CI NH Ar5 R11-22 2721 CI NH Ar6 R11-26 2683 CI NH Ar5 R11-23 2722 CI NH Ar6 R11-27 Line R Q Ar D Line R Q Ar D
2723 CI NH Ar6 R11-28 2762 CI NH AC A11-2a 2724 CI NH Ar6 R11-29 2763 Cl NH AC A11-2b 2725 CI NH Ar6 A11-la 2764 CI NH Ar7 A11-3a 2726 CI NH Ar6 A11-lb 2765 CI NH Ar7 A11-3b 2727 CI NH Ar6 A11-2a 2766 CI NH Ar8 R11-1 2728 CI NH Ar6 A11-2b 2767 CI NH Ar8 R11-2 2729 CI NH Ar6 A11-3a 2768 CI NH Ar8 R11-3 2730 CI NH Ar6 A11-3b 2769 CI NH Ar8 R11-4 2731 CI NH Ar7 R11-1 2770 CI NH Ar8 R11-5 2732 CI NH Ar7 R11-2 2771 CI NH Ar8 R11-6 2733 CI NH Ar7 R11-3 2772 CI NH Ar8 R11-7 2734 CI NH Ar7 R11-4 2773 CI NH Ar8 R11-8 2735 CI NH Ar7 R11-5 2774 CI NH Ar8 R11-9 2736 CI NH Ar7 R11-6 2775 CI NH Ar8 R11-10 2737 CI NH Ar7 R11-7 2776 CI NH Ar8 R11-11 2738 CI NH Ar7 R11-8 2777 CI NH Ar8 R11-12 2739 CI NH Ar7 R11-9 2778 CI NH Ar8 R11-13 2740 CI NH Ar7 R11-10 2779 CI NH Ar8 R11-14 2741 CI NH Ar7 R11-11 2780 CI NH Ar8 R11-15 2742 CI NH Ar7 R11-12 2781 CI NH Ar8 R11-16 2743 CI NH Ar7 R11-13 2782 CI NH Ar8 R11-17 2744 CI NH Ar7 R11-14 2783 CI NH Ar8 R11-18 2745 CI NH Ar7 R11-15 2784 CI NH Ar8 R11-19 2746 CI NH Ar7 R11-16 2785 CI NH Ar8 R11-20 2747 CI NH Ar7 R11-17 2786 CI NH Ar8 R11-21 2748 CI NH Ar7 R11-18 2787 CI NH Ar8 R11-22 2749 CI NH AC R11-19 2788 CI NH Ar8 R11-23 2750 CI NH Ar7 R11-20 2789 CI NH Ar8 R11-24 2751 CI NH Ar7 R11-21 2790 CI NH Ar8 R11-25 2752 CI NH AC R11-22 2791 CI NH Ar8 R11-26 2753 CI NH AC R11-23 2792 CI NH Ar8 R11-27 2754 CI NH AC R11-24 2793 CI NH Ar8 R11-28 2755 CI NH Ar7 R11-25 2794 CI NH Ar8 R11-29 2756 CI NH AC R11-26 2795 CI NH Ar8 A11-la 2757 CI NH AC R11-27 2796 CI NH Ar8 A11-1b 2758 CI NH Ar7 R11-28 2797 CI NH Ar8 A11-2a 2759 CI NH Ar7 R11-29 2798 CI NH Ar8 A11-2b 2760 CI NH Ar7 A11-la 2799 CI NH Ar8 A11-3a 2761 CI NH Ar7 A11-lb 2800 CI NH Ar8 A11-3b Line R Q Ar D Line R Q Ar D
2801 CI NH Ar9 R11-1 2840 CI NH Arl R11-5 2802 CI NH Ar9 R11-2 2841 Cl NH Arl R11-6 2803 CI NH Ar9 R11-3 2842 CI NH Arlo R11-7 2804 CI NH Ar9 R11-4 2843 CI NH Arlo R11-8 2805 CI NH Ar9 R11-5 2844 CI NH Arl R11-9 2806 CI NH Ar9 R11-6 2845 CI NH Arlo R11-10 2807 CI NH Ar9 R11-7 2846 CI NH Arlo R11-11 2808 CI NH Ar9 R11-8 2847 CI NH Arlo R11-12 2809 CI NH Ar9 R11-9 2848 CI NH Arlo R11-13 2810 CI NH Ar9 R11-10 2849 CI NH Arlo R11-14 2811 CI NH Ar9 R11-11 2850 CI NH Arlo R11-15 2812 CI NH Ar9 R11-12 2851 CI NH Arlo R11-16 2813 CI NH Ar9 R11-13 2852 CI NH Arlo R11-17 2814 CI NH Ar9 R11-14 2853 CI NH Arlo R11-18 2815 CI NH Ar9 R11-15 2854 CI NH Arlo R11-19 2816 CI NH Ar9 R11-16 2855 CI NH Arlo R11-20 2817 CI NH Ar9 R11-17 2856 CI NH Arlo R11-21 2818 CI NH Ar9 R11-18 2857 CI NH Arlo R11-22 2819 CI NH Ar9 R11-19 2858 CI NH Arlo R11-23 2820 CI NH Ar9 R11-20 2859 CI NH Arlo R11-24 2821 CI NH Ar9 R11-21 2860 CI NH Arlo R11-25 2822 CI NH Ar9 R11-22 2861 CI NH Arlo R11-26 2823 CI NH Ar9 R11-23 2862 CI NH Arlo R11-27 2824 CI NH Ar9 R11-24 2863 CI NH Arlo R11-28 2825 CI NH Ar9 R11-25 2864 CI NH Arlo R11-29 2826 CI NH Ar9 R11-26 2865 CI NH Arlo A11-la 2827 CI NH Ar9 R11-27 2866 CI NH Arl A11-lb 2828 CI NH Ar9 R11-28 2867 CI NH Arlo A11-2a 2829 CI NH Ar9 R11-29 2868 CI NH Arlo A11-2b 2830 CI NH Ar9 A11-la 2869 CI NH Arl A11-3a 2831 CI NH Ar9 A11-lb 2870 CI NH Arl A11-3b 2832 CI NH Ar9 A11-2a 2871 CI NH Aril R11-1 2833 CI NH Ar9 A11-2b 2872 CI NH Aril R11-2 2834 CI NH Ar9 A11-3a 2873 CI NH Aril R11-3 2835 CI NH Ar9 A11-3b 2874 CI NH Aril R11-4 2836 CI NH Arlo R11-1 2875 CI NH Aril R11-5 2837 CI NH Arlo R11-2 2876 CI NH Aril R11-6 2838 CI NH Arlo R11-3 2877 CI NH Aril R11-7 2839 CI NH Arlo R11-4 2878 CI NH Aril R11-8 Line R Q Ar D Line R Q Ar D
2879 CI NH Aril R11-9 2918 CI NH Ar12 R11-13 2880 CI NH Aril R11-10 2919 Cl NH Ar12 R11-14 2881 CI NH Aril R11-11 2920 CI NH Ar12 R11-15 2882 CI NH Aril R11-12 2921 CI NH Ar12 R11-16 2883 CI NH Aril R11-13 2922 CI NH Ar12 R11-17 2884 CI NH Aril R11-14 2923 CI NH Ar12 R11-18 2885 CI NH Aril R11-15 2924 CI NH Ar12 R11-19 2886 CI NH Aril R11-16 2925 CI NH Ar12 R11-20 2887 CI NH Aril R11-17 2926 CI NH Ar12 R11-21 2888 CI NH Aril R11-18 2927 CI NH Ar12 R11-22 2889 CI NH Aril R11-19 2928 CI NH Ar12 R11-23 2890 CI NH Aril R11-20 2929 CI NH Ar12 R11-24 2891 CI NH Aril R11-21 2930 CI NH Ar12 R11-25 2892 CI NH Aril R11-22 2931 CI NH Ar12 R11-26 2893 CI NH Aril R11-23 2932 CI NH Ar12 R11-27 2894 CI NH Aril R11-24 2933 CI NH Ar12 R11-28 2895 CI NH Aril R11-25 2934 CI NH Ar12 R11-29 2896 CI NH Aril R11-26 2935 CI NH Ar12 A11-la 2897 CI NH Aril R11-27 2936 CI NH Ar12 A11-lb 2898 CI NH Aril R11-28 2937 CI NH Ar12 A11-2a 2899 CI NH Aril R11-29 2938 CI NH Ar12 A11-2b 2900 CI NH Aril A11-la 2939 CI NH Ar12 A11-3a 2901 CI NH Aril A11-lb 2940 CI NH Ar12 A11-3b 2902 CI NH Aril A11-2a 2941 CI NCH3 Arl R11-1 2903 CI NH Aril A11-2b 2942 CI NCH3 Arl R11-2 2904 CI NH Aril A11-3a 2943 CI NCH3 Arl R11-3 2905 CI NH Aril A11-3b 2944 CI NCH3 Arl R11-4 2906 CI NH Ar12 R11-1 2945 CI NCH3 Arl R11-5 2907 CI NH Ar12 R11-2 2946 CI NCH3 Arl R11-6 2908 CI NH Ar12 R11-3 2947 CI NCH3 Arl R11-7 2909 CI NH Ar12 R11-4 2948 CI NCH3 Arl R11-8 2910 CI NH Ar12 R11-5 2949 CI NCH3 Arl R11-9 2911 CI NH Ar12 R11-6 2950 CI NCH3 Arl R11-10 2912 CI NH Ar12 R11-7 2951 CI NCH3 Arl R11-11 2913 CI NH Ar12 R11-8 2952 CI NCH3 Arl R11-12 2914 CI NH Ar12 R11-9 2953 CI NCH3 Arl R11-13 2915 CI NH Ar12 R11-10 2954 CI NCH3 Arl R11-14 2916 CI NH Ar12 R11-11 2955 CI NCH3 Arl R11-15 2917 CI NH Ar12 R11-12 2956 CI NCH3 Arl R11-16 Line R Q Ar D Line R Q Ar D
2957 CI NCH3 Arl R11-17 2996 CI NCH3 Ar2 R11-21 2958 CI NCH3 Arl R11-18 2997 Cl NCH3 Ar2 R11-22 2959 CI NCH3 Arl R11-19 2998 CI NCH3 Ar2 R11-23 2960 CI NCH3 Arl R11-20 2999 CI NCH3 Ar2 R11-24 2961 CI NCH3 Arl R11-21 3000 CI NCH3 Ar2 R11-25 2962 CI NCH3 Arl R11-22 3001 CI NCH3 Ar2 R11-26 2963 CI NCH3 Arl R11-23 3002 CI NCH3 Ar2 R11-27 2964 CI NCH3 Arl R11-24 3003 CI NCH3 Ar2 R11-28 2965 CI NCH3 Arl R11-25 3004 CI NCH3 Ar2 R11-29 2966 CI NCH3 Arl R11-26 3005 CI NCH3 Ar2 A11-la 2967 CI NCH3 Arl R11-27 3006 CI NCH3 Ar2 A11-lb 2968 CI NCH3 Arl R11-28 3007 CI NCH3 Ar2 A11-2a 2969 CI NCH3 Arl R11-29 3008 CI NCH3 Ar2 A11-2b 2970 CI NCH3 Arl A11-la 3009 CI NCH3 Ar2 A11-3a 2971 CI NCH3 Arl A11-lb 3010 CI NCH3 Ar2 A11-3b 2972 CI NCH3 Arl A11-2a 3011 CI NCH3 Ar3 R11-1 2973 CI NCH3 Arl A11-2b 3012 CI NCH3 Ar3 R11-2 2974 CI NCH3 Arl A11-3a 3013 CI NCH3 Ar3 R11-3 2975 CI NCH3 Arl A11-3b 3014 CI NCH3 Ar3 R11-4 2976 CI NCH3 Ar2 R11-1 3015 CI NCH3 Ar3 R11-5 2977 CI NCH3 Ar2 R11-2 3016 CI NCH3 Ar3 R11-6 2978 CI NCH3 Ar2 R11-3 3017 CI NCH3 Ar3 R11-7 2979 CI NCH3 Ar2 R11-4 3018 CI NCH3 Ar3 R11-8 2980 CI NCH3 Ar2 R11-5 3019 CI NCH3 Ar3 R11-9 2981 CI NCH3 Ar2 R11-6 3020 CI NCH3 Ar3 R11-10 2982 CI NCH3 Ar2 R11-7 3021 CI NCH3 Ar3 R11-11 2983 CI NCH3 Ar2 R11-8 3022 CI NCH3 Ar3 R11-12 2984 CI NCH3 Ar2 R11-9 3023 CI NCH3 Ar3 R11-13 2985 CI NCH3 Ar2 R11-10 3024 CI NCH3 Ar3 R11-14 2986 CI NCH3 Ar2 R11-11 3025 CI NCH3 Ar3 R11-15 2987 CI NCH3 Ar2 R11-12 3026 CI NCH3 Ar3 R11-16 2988 CI NCH3 Ar2 R11-13 3027 CI NCH3 Ar3 R11-17 2989 CI NCH3 Ar2 R11-14 3028 CI NCH3 Ar3 R11-18 2990 CI NCH3 Ar2 R11-15 3029 CI NCH3 Ar3 R11-19 2991 CI NCH3 Ar2 R11-16 3030 CI NCH3 Ar3 R11-20 2992 CI NCH3 Ar2 R11-17 3031 CI NCH3 Ar3 R11-21 2993 CI NCH3 Ar2 R11-18 3032 CI NCH3 Ar3 R11-22 2994 CI NCH3 Ar2 R11-19 3033 CI NCH3 Ar3 R11-23 2995 CI NCH3 Ar2 R11-20 3034 CI NCH3 Ar3 R11-24 Line R Q Ar D Line R Q Ar D
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3425 CI 0 Ar2 A11-la 3464 CI 0 Ar3 A11-3a 3426 CI 0 Ar2 A11-lb 3465 Cl 0 Ar4 A11-3b 3427 CI 0 Ar2 A11-2a 3466 CI 0 Ar4 R11-1 3428 CI 0 Ar2 A11-2b 3467 CI 0 Ar4 R11-2 3429 CI 0 Ar2 A11-3a 3468 CI 0 Ar4 R11-3 3430 CI 0 Ar2 A11-3b 3469 CI 0 Ar4 R11-4 3431 CI 0 Ar3 R11-1 3470 CI 0 Ar4 R11-5 3432 CI 0 Ar3 R11-2 3471 CI 0 Ar4 R11-6 3433 CI 0 Ar3 R11-3 3472 CI 0 Ar4 R11-7 3434 CI 0 Ar3 R11-4 3473 CI 0 Ar4 R11-8 3435 CI 0 Ar3 R11-5 3474 CI 0 Ar4 R11-9 3436 CI 0 Ar3 R11-6 3475 CI 0 Ar4 R11-10 3437 CI 0 Ar3 R11-7 3476 CI 0 Ar4 R11-11 3438 CI 0 Ar3 R11-8 3477 CI 0 Ar4 R11-12 3439 CI 0 Ar3 R11-9 3478 CI 0 Ar4 R11-13 3440 CI 0 Ar3 R11-10 3479 CI 0 Ar4 R11-14 3441 CI 0 Ar3 R11-11 3480 CI 0 Ar4 R11-15 3442 CI 0 Ar3 R11-12 3481 CI 0 Ar4 R11-16 3443 CI 0 Ar3 R11-13 3482 CI 0 Ar4 R11-17 3444 CI 0 Ar3 R11-14 3483 CI 0 Ar4 R11-18 3445 CI 0 Ar3 R11-15 3484 CI 0 Ar4 R11-19 3446 CI 0 Ar3 R11-16 3485 CI 0 Ar4 R11-20 3447 CI 0 Ar3 R11-17 3486 CI 0 Ar4 R11-21 3448 CI 0 Ar3 R11-18 3487 CI 0 Ar4 R11-22 3449 CI 0 Ar3 R11-19 3488 CI 0 Ar4 R11-23 3450 CI 0 Ar3 R11-20 3489 CI 0 Ar4 R11-24 3451 CI 0 Ar3 R11-21 3490 CI 0 Ar4 R11-25 3452 CI 0 Ar3 R11-22 3491 CI 0 Ar4 R11-26 3453 CI 0 Ar3 R11-23 3492 CI 0 Ar4 R11-27 3454 CI 0 Ar3 R11-24 3493 CI 0 Ar4 R11-28 3455 CI 0 Ar3 R11-25 3494 CI 0 Ar4 R11-29 3456 CI 0 Ar3 R11-26 3495 CI 0 Ar4 A11-la 3457 CI 0 Ar3 R11-27 3496 CI 0 Ar4 A11-1b 3458 CI 0 Ar3 R11-28 3497 CI 0 Ar4 A11-2a 3459 CI 0 Ar3 R11-29 3498 CI 0 Ar4 A11-2b 3460 CI 0 Ar3 A11-la 3499 CI 0 Ar4 A11-3a 3461 CI 0 Ar3 A11-1b 3500 CI 0 Ar4 A11-3b 3462 CI 0 Ar3 A11-2a 3501 CI 0 Ar5 R11-1 3463 CI 0 Ar3 A11-2b 3502 CI 0 Ar5 R11-2 Line R Q Ar D Line R Q Ar D
3503 CI 0 Ar5 R11-3 3542 CI 0 Ar6 R11-7 3504 CI 0 Ar5 R11-4 3543 Cl 0 Ar6 R11-8 3505 CI 0 Ar5 R11-5 3544 CI 0 Ar6 R11-9 3506 CI 0 Ar5 R11-6 3545 CI 0 Ar6 R11-10 3507 CI 0 Ar5 R11-7 3546 CI 0 Ar6 R11-11 3508 CI 0 Ar5 R11-8 3547 CI 0 Ar6 R11-12 3509 CI 0 Ar5 R11-9 3548 CI 0 Ar6 R11-13 3510 CI 0 Ar5 R11-10 3549 CI 0 Ar6 R11-14 3511 CI 0 Ar5 R11-11 3550 CI 0 Ar6 R11-15 3512 CI 0 Ar5 R11-12 3551 CI 0 Ar6 R11-16 3513 CI 0 Ar5 R11-13 3552 CI 0 Ar6 R11-17 3514 CI 0 Ar5 R11-14 3553 CI 0 Ar6 R11-18 3515 CI 0 Ar5 R11-15 3554 CI 0 Ar6 R11-19 3516 CI 0 Ar5 R11-16 3555 CI 0 Ar6 R11-20 3517 CI 0 Ar5 R11-17 3556 CI 0 Ar6 R11-21 3518 CI 0 Ar5 R11-18 3557 CI 0 Ar6 R11-22 3519 CI 0 Ar5 R11-19 3558 CI 0 Ar6 R11-23 3520 CI 0 Ar5 R11-20 3559 CI 0 Ar6 R11-24 3521 CI 0 Ar5 R11-21 3560 CI 0 Ar6 R11-25 3522 CI 0 Ar5 R11-22 3561 CI 0 Ar6 R11-26 3523 CI 0 Ar5 R11-23 3562 CI 0 Ar6 R11-27 3524 CI 0 Ar5 R11-24 3563 CI 0 Ar6 R11-28 3525 CI 0 Ar5 R11-25 3564 CI 0 Ar6 R11-29 3526 CI 0 Ar5 R11-26 3565 CI 0 Ar6 A11-la 3527 CI 0 Ar5 R11-27 3566 CI 0 Ar6 A11-1b 3528 CI 0 Ar5 R11-28 3567 CI 0 Ar6 A11-2a 3529 CI 0 Ar5 R11-29 3568 CI 0 Ar6 A11-2b 3530 CI 0 Ar5 A11-la 3569 CI 0 Ar6 A11-3a 3531 CI 0 Ar5 A11-1b 3570 CI 0 Ar6 A11-3b 3532 CI 0 Ar5 A11-2a 3571 CI 0 Ar7 R11-1 3533 CI 0 Ar5 A11-2b 3572 CI 0 Ar7 R11-2 3534 CI 0 Ar5 A11-3a 3573 CI 0 Ar7 R11-3 3535 CI 0 Ar5 A11-3b 3574 CI 0 Ar7 R11-4 3536 CI 0 Ar6 R11-1 3575 CI 0 Ar7 R11-5 3537 CI 0 Ar6 R11-2 3576 CI 0 Ar7 R11-6 3538 CI 0 Ar6 R11-3 3577 CI 0 Ar7 R11-7 3539 CI 0 Ar6 R11-4 3578 CI 0 Ar7 R11-8 3540 CI 0 Ar6 R11-5 3579 CI 0 Ar7 R11-9 3541 CI 0 Ar6 R11-6 3580 CI 0 Ar7 R11-10 Line R Q Ar D Line R Q Ar D
3581 CI 0 Ar7 R" -11 3620 CI 0 Ar8 R11-15 3582 CI 0 Ar7 R11-12 3621 Cl 0 Ar8 R11-16 3583 CI 0 Ar7 R11-13 3622 CI 0 Ar8 R11-17 3584 CI 0 Ar7 R11-14 3623 CI 0 Ar8 R11-18 3585 CI 0 Ar7 R11-15 3624 CI 0 Ar8 R11-19 3586 CI 0 Ar7 R11-16 3625 CI 0 Ar8 R11-20 3587 CI 0 Ar7 R11-17 3626 CI 0 Ar8 R11-21 3588 CI 0 Ar7 R11-18 3627 CI 0 Ar8 R11-22 3589 CI 0 Ar7 R11-19 3628 CI 0 Ar8 R11-23 3590 CI 0 Ar7 R11-20 3629 CI 0 Ar8 R11-24 3591 CI 0 Ar7 R11-21 3630 CI 0 Ar8 R11-25 3592 CI 0 Ar7 R11-22 3631 CI 0 Ar8 R11-26 3593 CI 0 Ar7 R11-23 3632 CI 0 Ar8 R11-27 3594 CI 0 Ar7 R11-24 3633 CI 0 Ar8 R11-28 3595 CI 0 Ar7 R11-25 3634 CI 0 Ar8 R11-29 3596 CI 0 Ar7 R11-26 3635 CI 0 Ar8 A11-la 3597 CI 0 Ar7 R11-27 3636 CI 0 Ar8 A11-lb 3598 CI 0 Ar7 R11-28 3637 CI 0 Ar8 A11-2a 3599 CI 0 Ar7 R11-29 3638 CI 0 Ar8 A11-2b 3600 CI 0 Ar7 A11-la 3639 CI 0 Ar8 A11-3a 3601 CI 0 Ar7 A11-lb 3640 CI 0 Ar8 A11-3b 3602 CI 0 Ar7 A11-2a 3641 CI 0 Ar9 R11-1 3603 CI 0 Ar7 A11-2b 3642 CI 0 Ar9 R11-2 3604 CI 0 Ar7 A11-3a 3643 CI 0 Ar9 R11-3 3605 CI 0 Ar7 A11-3b 3644 CI 0 Ar9 R11-4 3606 CI 0 Ar8 R11-1 3645 CI 0 Ar9 R11-5 3607 CI 0 Ar8 R11-2 3646 CI 0 Ar9 R11-6 3608 CI 0 Ar8 R11-3 3647 CI 0 Ar9 R11-7 3609 CI 0 Ar8 R11-4 3648 CI 0 Ar9 R11-8 3610 CI 0 Ar8 R11-5 3649 CI 0 Ar9 R11-9 3611 CI 0 Ar8 R11-6 3650 CI 0 Ar9 R11-10 3612 CI 0 Ar8 R11-7 3651 CI 0 Ar9 R11-11 3613 CI 0 Ar8 R11-8 3652 CI 0 Ar9 R11-12 3614 CI 0 Ar8 R11-9 3653 CI 0 Ar9 R11-13 3615 CI 0 Ar8 R11-10 3654 CI 0 Ar9 R11-14 3616 CI 0 Ar8 R11-11 3655 CI 0 Ar9 R11-15 3617 CI 0 Ar8 R11-12 3656 CI 0 Ar9 R11-16 3618 CI 0 Ar8 R11-13 3657 CI 0 Ar9 R11-17 3619 CI 0 Ar8 R11-14 3658 CI 0 Ar9 R11-18 Line R Q Ar D Line R Q Ar D
3659 CI 0 Ar9 R11-19 3698 CI 0 Arl R11-23 3660 CI 0 Ar9 R11-20 3699 Cl 0 Arl R11-24 3661 CI 0 Ar9 R11-21 3700 CI 0 Arlo R11-25 3662 CI 0 Ar9 R11-22 3701 CI 0 Arlo R11-26 3663 CI 0 Ar9 R11-23 3702 CI 0 Arl R11-27 3664 CI 0 Ar9 R11-24 3703 CI 0 Arlo R11-28 3665 CI 0 Ar9 R11-25 3704 CI 0 Arlo R11-29 3666 CI 0 Ar9 R11-26 3705 CI 0 Arlo A11-la 3667 CI 0 Ar9 R11-27 3706 CI 0 Arlo A11-lb 3668 CI 0 Ar9 R11-28 3707 CI 0 Arlo A11-2a 3669 CI 0 Ar9 R11-29 3708 CI 0 Arlo A11-2b 3670 CI 0 Ar9 A11-la 3709 CI 0 Arlo A11-3a 3671 CI 0 Ar9 A11-lb 3710 CI 0 Arlo A11-3b 3672 CI 0 Ar9 A11-2a 3711 CI 0 Arl 1 R11-1 3673 CI 0 Ar9 A11-2b 3712 CI 0 Arl 1 R11-2 3674 CI 0 Ar9 A11-3a 3713 CI 0 Arl 1 R11-3 3675 CI 0 Ar9 A11-3b 3714 CI 0 Arl 1 R11-4 3676 CI 0 Arlo R11-1 3715 CI 0 Arl 1 R11-5 3677 CI 0 Arlo R11-2 3716 CI 0 Arl 1 R11-6 3678 CI 0 Arlo R11-3 3717 CI 0 Arl 1 R11-7 3679 CI 0 Arlo R11-4 3718 CI 0 Arl 1 R11-8 3680 CI 0 Arlo R11-5 3719 CI 0 Arl 1 R11-9 3681 CI 0 Arlo R11-6 3720 CI 0 Arl 1 R11-10 3682 CI 0 Arlo R11-7 3721 CI 0 Arl 1 R11-11 3683 CI 0 Arlo R11-8 3722 CI 0 Arl 1 R11-12 3684 CI 0 Arlo R11-9 3723 CI 0 Arl 1 R11-13 3685 CI 0 Arl R11-10 3724 CI 0 Arl 1 R11-14 3686 CI 0 Arlo R11-11 3725 CI 0 Arl 1 R11-15 3687 CI 0 Arlo R11-12 3726 CI 0 Arl 1 R11-16 3688 CI 0 Arl R11-13 3727 CI 0 Arl 1 R11-17 3689 CI 0 Arl R11-14 3728 CI 0 Arl 1 R11-18 3690 CI 0 Arl R11-15 3729 CI 0 Arl 1 R11-19 3691 CI 0 Arlo R11-16 3730 CI 0 Arl 1 R11-20 3692 CI 0 Arl R11-17 3731 CI 0 Arl 1 R11-21 3693 CI 0 Arl R11-18 3732 CI 0 Aril R11-22 3694 CI 0 Arlo R11-19 3733 CI 0 Arl 1 R11-23 3695 CI 0 Arlo R11-20 3734 CI 0 Aril R11-24 3696 CI 0 Arlo R11-21 3735 CI 0 Arl 1 R11-25 3697 CI 0 Arlo R11-22 3736 CI 0 Arl 1 R11-26 Line R Q Ar D Line R Q Ar D
3737 CI 0 Aril R11-27 3759 CI 0 Ar12 R11-14 3738 CI 0 Aril R11-28 3760 CI 0 Ar12 R11-15 3739 CI 0 Aril R11-29 3761 CI 0 Ar12 R11-16 3740 Cl 0 Ar11 pol_la 3762 Cl 0 Ar12 R11-17 3741 Cl 0 Aril A11-lb 3763 Cl 0 Ar12 R11-18 3742 Cl 0 Ar11 18,11-2a 3764 Cl 0 Ar12 R11-19 3743 Cl 0 Ar11 18,11-2b 3765 Cl 0 Ar12 R11-20 3744 Cl 0 Ar11 18,11-3a 3766 Cl 0 Ar12 R11-21 3745 Cl 0 Ar11 18,11-3b 3767 Cl 0 Ar12 R11-22 3746 Cl 0 Ar12 R11-1 3768 Cl 0 Ar12 R11-23 3747 Cl 0 Ar12 R11-2 3769 Cl 0 Ar12 R11-24 3748 Cl 0 Ar12 R11-3 3770 Cl 0 Ar12 R11-25 3749 Cl 0 Ar12 R11-4 3771 Cl 0 Ar12 R11-26 3750 Cl 0 Ar12 R11-5 3772 Cl 0 Ar12 R11-27 3751 Cl 0 Ar12 R11-6 3773 Cl 0 Ar12 R11-28 3752 Cl 0 Ar12 R11-7 3774 Cl 0 Ar12 R11-29 3753 Cl 0 Ar12 R11-8 3775 Cl 0 Ar12 A11-la 3754 Cl 0 Ar12 R11-9 3776 Cl 0 Ar12 A11-lb 3755 Cl 0 Ar12 R11-10 3777 Cl 0 Ar12 18,11-2a 3756 Cl 0 Ar12 R11-11 3778 Cl 0 Ar12 18,11-2b 3757 Cl 0 Ar12 R11-12 3779 Cl 0 Ar12 18,11-3a 3758 Cl 0 Ar12 R11-13 3780 Cl 0 Ar12 18,11-3b As used herein, the term "compound(s) of the present invention" or "compound(s) according to the invention" refers to the compound(s) of formula (I) as defined above, which are also referred to as "compound(s) of formula l" or "compound(s) l" or "formula I compound(s)", and includes their salts, tautomers, stereoisomers, and N-oxides.
The present invention also relates to a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after. Preferred are binary mixtures of one com-pound of the present invention as component I with one mixing partner as defined herein after as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, prefera-bly from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, particularly preferably from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component ll may be used.
Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acari-cides, fungicides, herbicides, plant growth regulators, fertilizers, and the like. Preferred mixing part-ners are insecticides, nematicides and fungicides.
The following list M of pesticides, grouped and numbered according the Mode of Action Classifi-cation of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the present invention can be used and with which potential synergistic effects might be pro-duced, is intended to illustrate the possible combinations, but not to impose any limitation:
M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A
carbamates, for example al-dicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, metho-myl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1B organophosphates, for example acephate, aza-methiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, dia-zinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, etho-prophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl 0- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecar-bam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;
M.2. GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine com-pounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for exam-pie ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
M.3 Sodium channel modulators from the class of M.3A pyrethroids, for example acrinathrin, alle-thrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cyper-methrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fen-valerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluth-rin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyre-thrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and trans-fluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;
M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of M.4A
neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.2: (2E+14(6-Chloropyridin-3-yhmethylFV-nitro-2-pen-tylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yhmethy1]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; or from the class M.4B
nicotine;
M.5 Nicotinic acetylcholine receptor allosteric activators from the class of spinosyns, for example spinosad or spinetoram;
M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues as hydroprene, ki-noprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
M.8 miscellaneous non-specific (multi-site) inhibitors, for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.80 sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
M.9 Selective homopteran feeding blockers, for example M.9B pymetrozine, or M.90 flonicamid;
M.10 Mite growth inhibitors, for example M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
M.11 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacil-lus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is-raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp.
kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;
M.12 Inhibitors of mitochondria! ATP synthase, for example M.12A
diafenthiuron, or M.12B organ-otin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.120 propargite, or M.12D
tetradifon;
M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, for example chlorfenapyr, DNOC or sulfluramid;
M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for example nereistoxin ana-logues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
M.16 Inhibitors of the chitin biosynthesis type 1, as for example buprofezin;
M.17 Moulting disruptors, Dipteran, as for example cyromazine;
M.18 Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufe-nozide, halofenozide, fufenozide or chromafenozide;
M.19 Octopamin receptor agonists, as for example amitraz;
M.20 Mitochondria! complex III electron transport inhibitors, for example M.20A hydramethylnon, or M.20B acequinocyl, or M.200 fluacrypyrim;
M.21 Mitochondria! complex I electron transport inhibitors, for example M.21A
METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen-pyrad, or M.21B rotenone;
M.22 Voltage-dependent sodium channel blockers, for example M.22A indoxacarb, or M.22B met-aflumizone, or M.226.1: 242-(4-Cyanopheny1)-143-(trifluoromethyl)phenyl]ethylideneFN44-(difluo-romethoxy)phenylFhydrazinecarboxamide or M.226.2: N-(3-Chloro-2-methylpheny1)-2-[(4-chloro-phenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methyleneFhydrazinecarboxamide;
M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat;
M.24 Mitochondria! complex IV electron transport inhibitors, for example M.24A
phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
M.25 Mitochondrial complex ll electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendiamide, chlorantraniliprole (rynaxypyre), cyantraniliprole (cyazypyre), tetraniliprole, or the phthalamide compounds M.28.1: (R)-3-Chlor-N1-{2-methy1-4-[1,2,2,2 ¨tetrafluor-1-(trifluormethypethyl]pheny1}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid and M.28.2: (S)-3-Chlor-N1-{2-methy1-4-[1,2,2,2 ¨
tetrafluor-1-(trifluormethypethyl]pheny1}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, or the com-pound M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]pheny1}-1-(3-chlorpyridin-2-y1)-1H-pyrazole-5-carboxamide (proposed ISO name:
cyclaniliprole), or the com-pound M.28.4: methy1-243,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-y1)-1H-pyrazol-5-yl]carbony1}-amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; or a compound selected from M.28.5a) to M.28.5d) and M.28.5h) to M.28.51): M.28.5a) N44,6-dichloro-2-Rdiethyl-lambda-4-sulfanylidene)car-bamoy1Fphenyl]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyppyrazole-3-carboxamide; M.28.5b) N44-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyI]-6-methyl-pheny1]-2-(3-chloro-2-pyridy1)-5-(tri-fluoromethyl)pyrazole-3-carboxamide; M.28.5c) N44-chloro-2-[(di-2-propyl-lambda-4-sulfanyli-dene)carbamoyI]-6-methyl-pheny1]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5d) N44,6-dichloro-2-Rdi-2-propyl-lambda-4-sulfanylidene)carbamoy1Fphenyl]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyppyrazole-3-carboxamide; M.28.5h) N-[4,6-dibromo-2-Rdiethyl-lambda-4-sulfanylidene)carbamoy1Fphenyl]-2-(3-chloro-2-pyridy1)-5-(trifluoromethyppyrazole-3-carboxamide;
M.28.5i) N42-(5-Amino-1,3,4-thiadiazol-2-y1)-4-chloro-6-methylpheny1]-3-bromo-1-(3-chloro-2-pyri-diny1)-1H-pyrazole-5-carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridiny1)-N42,4-dichloro-6-[[(1-cyano-1-methylethypamino]carbonyl]pheny1]-1H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)pheny1]-1-(3,5-dichloro-2-pyridy1)-1H-pyrazole-5-carboxamide;
M.28.51) N44-Chloro-2-[[(1,1-dimethylethypamino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridi-ny1)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or M.28.6: cyhalodiamide; or;
M.29. insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromo-propylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or the compounds M.29.3: 11-(4-chloro-2,6-dimethylphenyI)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, or the compound M.29.4: 3-(4'-fluoro-2,4-dimethylbipheny1-3-y1)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, or the compound M.29.5: 142-fluoro-4-methy1-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or a compound selected from the of M.29.6, wherein the compound M.29.6a) to M.29.6k): M.29.6a) (E/Z)-N41-[(6-chloro-3-pyridyl)methy1]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6b) (E/Z)-N-[14(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6c) (E/Z)-2,2,2-trifluoro-N41-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;
M.29.6d) (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyI]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6e) (E/Z)-N4141-(6-chloro-3-pyridypethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6f) (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyI]-2-pyridylidene]-2,2-difluoro-acetamide; M.29.6g) (E/Z)-2-chloro-N41-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; M.29.6h) (E/Z)-N41-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; M.29.6i) (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.); M.29.6j) N41-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide; or M.29.6k) N41-[(6-chloro-3-pyridyl)methyl]-2-pyridyli-dene]-2,2,2-trifluoro-N'-isopropyl-acetamidine; or the compounds M.29.8: fluazaindolizine; or the compounds M.29.9.a): 445-(3,5-dichloropheny1)-5-(trifluoromethyl)-4H-isoxazol-3-y1]-2-methyl-N-(1-oxothietan-3-yObenzamide; or M.29.9.b): fluxametamide; or M.29.10: 5[342,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; or a compound selected from the of M.29.11, wherein the compound M.29.11b) to M.29. lip):
M.29.11.b) 3-(benzoylmethylamino)-N42-bromo-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propy1]-6-(trifluoromethyl)pheny1]-2-fluoro-benzamide; M.29.11.c) 3-(benzoylmethylamino)-2-fluoro-N42-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoromethyl)phenylFbenzamide; M.29.11.d) N43-[[[2-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoromethyl)phenyl]amino]car-bonyl]pheny1FN-methyl-benzamide; M.29.11.e) N43-[[[2-bromo-441,2,2,2-tetrafluoro-1-(trifluorome-thypethy1]-6-(trifluoromethyl)phenyl]amino]carbony1]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;
M.29.11.f) 4-fluoro-N42-fluoro-3-E2-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoro-methyl)phenyl]amino]carbonyl]pheny1FN-methyl-benzamide; M.29.11.g) 3-fluoro-N42-fluoro-3-[[[2-iodo-441,2,2,2-tetrafluoro-1-(trifluoromethypethy1]-6-(trifluoromethyl)phenyl]amino]carbonyl]pheny1]-N-methyl-benzamide; M.29.11.h) 2-chloro-N43-[[[2-iodo-441,2,2,2-tetrafluoro-1-(trifluorome-thypethy1]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenylF 3-pyridinecarboxamide; M.29.11.i) 4-cyano-N42-cyano-54[2,6-dibromo-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]car-bamoyl]phenyI]-2-methyl-benzamide; M.29.11.j) 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]pheny1]-2-fluoro-benzamide;
M.29.11.k) N454[2-chloro-6-cyano-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]car-bamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.11.I) N454[2-bromo-6-chloro-442,2,2-trifluoro-1-hydroxy-1-(trifluoromethypethyl]phenyl]carbamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.11.m) N454[2-bromo-6-chloro-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)pro-pyl]phenyl]carbamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.29.11.n) 4-cyano-N42-cy-ano-54[2,6-dichloro-441,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]pheny1]-2-methyl-benzamide; M.29.11.o) 4-cyano-N42-cyano-54[2,6-dichloro-441,2,2,2-tetrafluoro-1-(trifluo-romethypethyl]phenyl]carbamoyl]pheny1]-2-methyl-benzamide; M.29.11.p) N454[2-bromo-6-chloro-441,2,2,2-tetrafluoro-1-(trifluoromethypethyl]phenyl]carbamoy1]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or a compound selected from the of M.29.12, wherein the compound M.29.12a) to M.29.12m):
M.29.12.a) 2-(1,3-Dioxan-2-y1)-642-(3-pyridiny1)-5-thiazoly1Fpyridine;
M.29.12.b) 24642-(5-Fluoro-3-pyridiny1)-5-thiazoly1]-2-pyridiny1]-pyrimidine; M.29.12.c) 24642-(3-Pyridiny1)-5-thiazoly1]-2-pyridi-ny1]-pyrimidine; M.29.12.d) N-Methylsulfony1-642-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;
M.29.12.e) N-Methylsulfony1-642-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.29.12.f) N-Ethyl-N44-methyl-2-(3-pyridyl)thiazol-5-y1]-3-methylthio-propanamide; M.29.12.g) N-Methyl-N-[4-methyl-2-(3-pyridy0thiazol-5-y1]-3-methylthio-propanamide; M.29.12.h) N,2-Dimethyl-N44-methy1-2-(3-pyridyl)thiazol-5-y1]-3-methylthio-propanamide; M.29.12.i) N-Ethy1-2-methyl-N44-methy1-2-(3-pyridyl)thiazol-5-y1]-3-methylthio-propanamide; M.29.12.j) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN-ethyl-2-methyl-3-methylthio-propanamide; M.29.12.k) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN,2-di-methyl-3-methylthio-propanamide; M.29.12.1) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN-methyl-3-me-thylthio-propanamide; M.29.12.m) N44-Chloro-2-(3-pyridyl)thiazol-5-y1FN-ethyl-3-methylthio-pro-panamide; or the compounds M.29.14a) 1-[(6-Chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methy1-8-nitro-im-idazo[1,2-a]pyridine; or M.29.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hex-ahydroimidazo[1,2-a]pyridin-5-ol; or the compounds M.29.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1-(1,2-dimethylpropy1)-N-ethy1-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.16c) N,5-di-methyl-N-pyridazin-4-y1-1-(2,2,2-trifluoro-1-methyl-ethyppyrazole-4-carboxamide; M.29.16d) 141-(1-cyanocyclopropypethy1]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16e) N-ethyl-1-(2-fluoro-1-methyl-propy1)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16f) 1-(1,2-dimethylpropyI)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.1 6g) 141-(1-cya-nocyclopropypethy1FN,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.16h) N-methy1-1-(2-fluoro-1-methyl-propy1]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
M.29.1 6i) 1-(4,4-difluorocyclohexyl)-N-ethy1-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
or M.29.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, or M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j):
M.29.17a) N-(1-meth-ylethyl)-2-(3-pyridiny1)-2H-indazole-4-carboxamide; M.29.1 7b) N-cyclopropy1-2-(3-pyridiny1)-2H-in-dazole-4-carboxamide; M.29.17c) N-cyclohexy1-2-(3-pyridiny1)-2H-indazole-4-carboxamide;
M.29.17d) 2-(3-pyridiny1)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;
M.29. 17e) 2-(3-pyridi-nyI)-N-[(tetrahydro-2-furanyl)methy1]-2H-indazole-5-carboxamide; M.29.17f) methyl 24[2-(3-pyridi-ny1)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate; M.29.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridiny1)-2H-indazole-5-carboxamide; M.29.1 7h) N-(2,2-difluoropropyI)-2-(3-pyridiny1)-2H-in-dazole-5-carboxamide; M.29.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carbox-amide; M.29.1 7j) N-[(5-methy1-2-pyrazinyl)methyl]-2-(3-pyridiny1)-2H-indazole-5-carboxamide, or M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d):
M.29.18a) N43-chloro-1-(3-pyridyl)pyrazol-4-y1FN-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; M.29.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-y1]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide; M.29.18c) N43-chloro-1-(3-pyridyl)pyrazol-4-y1]-3-[(2,2-difluorocyclopropyl)methylsulfany1]-N-ethyl-propana-mide; M.29.18d) N-[3-chloro-1-(3-pyridyl)pyrazol-4-y1]-3-[(2,2-difluorocyclopropyl)methylsulfiny1]-N-ethyl-propanamide; or the compound M.29.19 sarolaner, or the compound M.29.20 lotilaner.
The commercially available compounds of the M listed above may be found in The Pesticide Man-ual, 16th Edition, C. MacBean, British Crop Protection Council (2013) among other publications.
.. The online Pesticide Manual is updated regularly and is accessible through http://bcpcdata.com/pesticide-manual.html.
Another online data base for pesticides providing the ISO common names is http://www.alan-wood.net/pesticides.
The M.4 neonicotinoid cycloxaprid is known from W02010/069266 and W02011/069456, the ne-onicotinoid M.4A.2, sometimes also to be named as guadipyr, is known from W02013/003977, and the neonicotinoid M.4A.3 (approved as paichongding in China) is known from W02007/101369.
The metaflumizone analogue M.226.1 is described in CN10171577 and the analogue M.226.2 in CN102126994. The phthalamides M.28.1 and M.28.2 are both known from W02007/101540. The anthranilamide M.28.3 is described in W02005/077934. The hydrazide compound M.28.4 is de-scribed in W02007/043677. The anthranilamides M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, W02013/024009 and W02013/024010, the anthranilamide M.28.5i) is de-scribed in W02011/085575, M.28.5j) in W02008/134969, M.28.5k) in U52011/046186 and M.28.51) in W02012/034403. The diamide compound M.28.6 can be found in W02012/034472.
The spiro-ketal-substituted cyclic ketoenol derivative M.29.3 is known from W02006/089633 and the bi-phenyl-substituted spirocyclic ketoenol derivative M.29.4 from W02008/067911.
The triazoylphen-ylsulfide M.29.5 is described in W02006/043635, and biological control agents on the basis of ba-cillus firmus are described in W02009/124707. The compounds M.29.6a) to M.29.6i) listed under M.29.6 are described in W02012/029672, and M.29.6j) and M.29.6k) in W02013/129688. The ne-maticide M.29.8 is known from W02013/055584. The isoxazoline M.29.9.a) is described in W02013/050317. The isoxazoline M.29.9.b) is described in W02014/126208. The pyridalyl-type analogue M.29.10 is known from W02010/060379. The carboxamides broflanilide and M.29.11.b) to M.29.11.h) are described in W02010/018714, and the carboxamides M.29.11i) to M.29.11.p) in W02010/127926. The pyridylthiazoles M.29.12.a) to M.29.12.c) are known from W02010/006713, M.29.12.d) and M.29.12.e) are known from W02012/000896, and M.29.12.f) to M.29.12.m) from W02010/129497. The compounds M.29.14a) and M.29.14b) are known from W02007/101369.
The pyrazoles M.29.16.a) to M.29.16h) are described in W02010/034737, W02012/084670, and W02012/143317, respectively, and the pyrazoles M.29.16i) and M.29.16j) are described in US
61/891437. The pyridinylindazoles M.29.17a) to M.29.17.j) are described in W02015/038503. The pyridylpyrazoles M.29.18a) to M.29.18d) are described in U52014/0213448. The isoxazoline M.29.19 is described in W02014/036056. The isoxazoline M.29.20 is known from W02014/090918.
The following list of fungicides, in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:
A) Respiration inhibitors - Inhibitors of complex III at Q0 site (e. g. strobilurins):
azoxystrobin (A.1.1), coumethoxy-strobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), man-destrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxy.strobin (A.1.13), pyra-clostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichloropheny1)-1-methyl-allylideneaminooxymethyl)-pheny1)-2-methoxyimino-N-methyl-ac-etamide (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21), methyl-N42-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-meth-oxy-carbamate (A.1.22), 1-[3-chloro-2-[[1-(4-chloropheny1)-1H-pyrazol-3-yl]oxymethyl]pheny1]-4-me-thyl-tetrazol-5-one (A.1.23), 143-bromo-24[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]pheny1]-4-me-thyl-tetrazol-5-one (A.1.24), 1424[1-(4-chlorophenyl)pyrazol-3-yl]oxymethy1]-3-methyl-pheny1]-4-methyl-tetrazol-5-one (A.1.25), 1424[1-(4-chlorophenyl)pyrazol-3-yl]oxymethy1]-3-fluoro-pheny1]-4-methyl-tetrazol-5-one (A.1.26), 1424[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethy1]-3-fluoro-pheny1]-4-methyl-tetrazol-5-one (A.1.27), 1424[4-(4-chlorophenyl)thiazol-2-yl]oxymethy1]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.28), 143-chloro-24[4-(p-tolypthiazol-2-yl]oxymethyl]pheny1]-4-methyl-tetrazol-5-one (A.1.29), 1-[3-cyclopropy1-2-[[2-methy1-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phe-ny1]-4-methyl-tetrazol-5-one (A.1.30), 143-(difluoromethoxy)-24[2-methy1-4-(1-methylpyrazol-3-yOphenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1.31), 1-methy1-443-methy1-2-[[2-methyl-4-(1-methylpyrazol-3-y1)phenoxy]methyl]phenyl]tetrazol-5-one (A.1.32), 1-methy1-443-methy1-2-[[143-(trifluoromethyl)phenylFethylideneamino]oxymethyl]phenyl]tetrazol-5-one (A.1.33), (22E)-541-(2,4-dichlorophenyOpyrazol-3-y1Foxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2 E)-5-[1-(4-chlorophenyOpyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), (Z,2 541-(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.36), - inhibitors of complex III at Q, site: cyazofamid (A.2.1), amisulbrom (A.2.2), [(3S,6S,7R,8R)-8-benzy1-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), [(3S,6S,7R,8R)-8-benzy1-3-[[3-(acetoxymethoxy)-4-methoxy-pyri-dine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.4), [(3S,6S,7R,8R)-8-benzy1-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-me-thy1-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.5), [(3S,6S,7R,8R)-8-benzy1-34[3-(1,3-benzodioxo1-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methy1-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.6); (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)car-bonyl]amino]-6-methy1-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-y12-methylpropanoate (A.2.7), (3S,6S,7R,8R)-8-benzy1-343-[(isobutyryloxy)methoxy]-4-methoxypicolinamido]-6-methy1-4,9-dioxo-1,5-dioxonan-7-ylisobutyrate (A.2.8);
- inhibitors of complex!! (e. g. carboxamides): benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), me-pronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobipheny1-2-y1)-3-difluoromethy1-1-methy1-1H-pyrazole-4-carboxamide (A.3.19), N-(2-(1,3,3-trimethyl-buty1)-pheny1)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide (A.3.20), 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yOpyrazole-4-carboxamide (A.3.21), 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yOpy-razole-4-carboxamide (A.3.22), 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.23), 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yOpyrazole-4-carboxamide (A.3.24), 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), N-(7-fluoro-1,1,3-trimethyl-indan-4-yI)-1,3-dimethyl-pyrazole-4-carboxamide (A.3.26), N42-(2,4-dichloropheny1)-2-methoxy-1-methyl-ethy1]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide (A.3.27);
- other respiration inhibitors (e. g. complex I, uncouplers): diflumetorim (A.4.1), (5,8-difluoro-quinazolin-4-y1)-{242-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenylFethyl}-amine (A.4.2); nitro-phenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferim-zone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); and silthiofam (A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides) - 014 demethylase inhibitors (DMI fungicides): triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobu-trazole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simecon-azole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 1-Vek(2S;3A)-3-(2-chloropheny1)-2-(2,4-difluoropheny1)-oxiranylmethy1]-5-thiocyanato-1H41,2,41triazolo (B.1.31), 2-Vek(2S;3R)-3-(2-chloro-pheny1)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol (B.1.32), 242-chloro-4-(4-chlorophenoxy)pheny1]-1-(1,2,4-triazol-1-y1)pentan-2-ol (B.1.33), 144-(4-chlorophenoxy)-2-(trifluoro-methyl)pheny1]-1-cyclopropy1-2-(1,2,4-triazol-1-yl)ethanol (B.1.34), 244-(4-chlorophenoxy)-2-(trifluo-romethyl)pheny1]-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.35), 242-chloro-4-(4-chlorophenoxy)pheny1]-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.36), 244-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.37), 244-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.38), 242-chloro-4-(4-chlorophenoxy)pheny1]-3-methyl-1-(1,2,4-triazol-1-y1)butan-2-ol (B.1.39), 244-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)pentan-2-01(6.1.40), 244-(4-fluorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.41), 2[2-chloro-4-(4-chlorophenoxy)pheny1]-1-(1,2,4-triazol-1-y1)pent-3-yn-2-ol (B.1.51); imid-azoles: imazalil (B.1.42), pefurazoate (B.1.43), prochloraz (B.1.44), triflumizol (B.1.45); pyrimidines, pyridines and piperazines: fenarimol (B.1.46), nuarimol (B.1.47), pyrifenox (B.1.48), triforine (B.1.49), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenypisoxazol-4-y1]-(3-pyridyl)methanol (B.1.50);
- Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox-amine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1);
C) Nucleic acid synthesis inhibitors - phenylamides or acyl amino acid fungicides: benalaxyl (0.1.1), benalaxyl-M (0.1.2), kiral-axyl (0.1.3), metalaxyl (0.1.4), metalaxyl-M (mefenoxam, 0.1.5), ofurace (0.1.6), oxadixyl (0.1.7);
- others: hymexazole (0.2.1), octhilinone (0.2.2), oxolinic acid (0.2.3), bupirimate (0.2.4), 5-fluorocytosine (0.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (0.2.6), 5-fluoro-2-(4-fluorophe-nylmethoxy)pyrimidin-4-amine (0.2.7);
D) Inhibitors of cell division and cytoskeleton - tubulin inhibitors, such as benzimidazoles, thiophanates: benomyl (D1.1), carbendazim (D1.2), fuberidazole (D1.3), thiabendazole (D1.4), thiophanate-methyl (D1.5);
triazolopyrimidines:
5-chloro-7-(4-methylpiperidin-1-y1)-6-(2,4,6-trifluoropheny1)41,2,41triazolo[1,5-a]pyrimidine (D1.6);
- other cell division inhibitors: diethofencarb (D2.1), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);
E) Inhibitors of amino acid and protein synthesis - methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
- protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydro-chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);
F) Signal transduction inhibitors - MAP! histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fenpiclonil (F.1.5), fludioxonil (F.1.6);
- G protein inhibitors: quinoxyfen (F.2.1);
G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
- lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1-(1-(4-cyano-phenyhethanesulfony1)-but-2-y1) carbamic acid-(4-fluorophenyl) ester (G.3.8);
- compounds affecting cell membrane permeability and fatty acides:
propamocarb (G.4.1);
- fatty acid amide hydrolase inhibitors: oxathiapiprolin (G.5.1), 2-{342-(1-{[3,5-bis(difluorome-thy1-1H-pyrazol-1-yl]acetyl}piperidin-4-y1)-1,3-thiazol-4-y1]-4,5-dihydro-1,2-oxazol-5-yl}phenyl me-thanesulfonate (G.5.2), 2-{342-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-y1) 1,3-thiazol-4-y1]-4,5-dihydro-1,2-oxazol-5-y1}-3-chlorophenyl methanesulfonate (G.5.3);
H) Inhibitors with Multi Site Action - inorganic active substances: Bordeaux mixture (H.1.1), copper acetate (H.1.2), copper hy-droxide (H.1.3), copper oxychloride (H.1.4), basic copper sulfate (H.1.5), sulfur (H.1.6);
- thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
- organochlorine compounds (e. g. phthalimides, sulfamides, chloronitriles): anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11), N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide (H.3.12);
- guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethy1-1H,5H41,41dithiino[2,3-c:5,6-cldipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10);
1) Cell wall synthesis inhibitors - inhibitors of glucan synthesis: validamycin (1.1.1), polyoxin B (1.1.2);
- melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);
J) Plant defence inducers - acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), potassium or sodium bicarbonate (J.1.9);
K) Unknown mode of action - bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.7), difenzoquat (K.1.8), difenzoquat-methylsulfate (K.1.9), diphenylamin (K.1.10), fenpyrazamine (K.1.11), flumetover (K.1.12), flusulfamide (K.1.13), flutianil (K.1.14), methasulfocarb (K.1.15), nitrapyrin (K.1.16), nitrothal-isopropyl (K.1.18), oxathiapiprolin (K.1.19), tolprocarb (K.1.20), oxin-copper (K.1.21), proquinazid (K.1.22), tebufloquin (K.1.23), tecloftalam (K.1.24), triazoxide (K.1.25), 2-butoxy-6-iodo-3-propylchromen-4-one (K.1.26), 243,5-bis(difluoromethyl)-1H-pyrazol-1-y1]-144-(4-{542-(prop-2-yn-1-yloxy)pheny1]-4,5-dihydro-1,2-oxazol-3-y1}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1.27), 243,5-bis(difluoromethyl)-1H-pyrazol-1-y1]-144-(4-{542-fluoro-6-(prop-2-yn-1-yloxy)pheny1]-4,5-dihydro-1,2-oxazol-3-y1}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1.28), 243,5-bis(difluoromethyl)-1H-pyrazol-1-y1]-144-(4-{542-chloro-6-(prop-2-yn-1-yloxy)pheny1]-4,5-dihydro-1,2-oxazol-3-y1}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (K.1.29), N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-pheny1)-methyl)-2-phenyl acetamide (K.1.30), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-pheny1)-N-ethyl-N-methyl formamidine (K.1.31), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-pheny1)-N-ethyl-N-methyl formamidine (K.1.32), N'-(2-methy1-5-trifluoromethy1-4-(3-trimethylsilanyl-propoxy)-pheny1)-N-ethyl-N-methyl formamidine (K.1.33), N'-(5-difluoromethy1-2-methy1-4-(3-trimethylsilanyl-propoxy)-pheny1)-N-ethyl-N-methyl formamidine (K.1.34), methoxy-acetic acid 6-tert-buty1-8-fluoro-2,3-dimethyl-quinolin-4-ylester (K.1.35), 345-(4-methylpheny1)-2,3-dimethyl-isoxazolidin-3-y1Fpyri-dine (K.1.36), 345-(4-chloro-pheny1)-2,3-dimethyl-isoxazolidin-3-y1Fpyridine (pyrisoxazole) (K.1.37), N-(6-methoxy-pyridin-3-y1) cyclopropanecarboxylic acid amide (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-y1)-2-methy1-1H-benzoimidazole (K.1.39), 2-(4-chloro-pheny1)-N44-(3,4-dimethoxy-pheny1)-isoxazol-5-y1]-2-prop-2-ynyloxy-acetamide, ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-eno-ate (K.1.40), picarbutrazox (K.1.41), pentyl N46-[[(Z)-[(1-methyltetrazol-5-y1)-phenyl-methylene]ami-no]oxymethy1]-2-pyridyl]carbamate (K.1.42), 242-[(7,8-difluoro-2-methy1-3-quinolypoxy]-6-fluoro-phenyl]propan-2-ol (K.1.43), 2[2-fluoro-6-[(8-fluoro-2-methy1-3-quinolypoxy]phen-yl]propan-2-ol (K.1.44), 3-(5-fluoro-3,3,4,4-tetramethy1-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.45), 3-(4,4-difluoro-3,3-dimethy1-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.46), 3-(4,4,5-trifluoro-3,3-dimethy1-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.47), 9-fluoro-2,2-dimethy1-5-(3-quinoly1)-3H-1,4-benzoxa-zepine (K.1.48).
The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
The fungicides described by IUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A
226 917; EP-A 243 970; EP-A 256 503; EP-A 428941; EP-A 532 022; EP-A 1 028 125; EP-A
1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE
10021412;
DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO
99/24413;
WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358;
WO 02/22583; WO 02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286;
WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 04/83193;
WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO 05/87772; WO
05/87773;
WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 11/028657, W02012/168188, WO 2007/006670, WO 2011/77514; W013/047749, WO 10/069882, WO
13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/024010 and WO 13/047441, WO 13/162072, WO 13/092224, WO
11/135833).
The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof. The term "pesticidally effective amount" is defined below.
The compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Mono-graph No.
2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and Grube-mann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports D5243, T&F Informa, London, 2005.
Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi-ers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac-tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al-kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-ihexanol; glycols;
DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch;
fertilizers, e.g.
ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1:
Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl-sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl-inaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox-ylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Exam-pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-oxylates.
Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Exam-pies of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries.
Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports D5256, T&F
Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer-rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g.
alcohols) up to 100 wt%.
The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC) 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e. g. polyvi-nylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g.
cyclohexanone). Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC) 15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES) 5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt%
water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS) In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g.
extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with ad-dition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dis-persion or solution of the active substance.
viii) Gel (GW, GF) In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt%
thickener (e.g. car-boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub-stance.
Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME) 5-20 wt% of a compound I according to the invention are added to 5-30 wt%
organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi-cal initiator results in the formation of poly(meth)acrylate microcapsules.
Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insolu-ble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
diphenylme-thene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
The addition of a polyamine (e.g. hexamethylenediamine) results in the for-mation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS
composition.
xi) Dustable powders (DP, DS) 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
xii) Granules (GR, FG) 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
xiii) Ultra-low volume liquids (UL) 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt%
bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% col-orants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably be-tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100%
(according to NMR spectrum).
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g.
herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions com-prising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
The user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the in-vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, either individual components of the composition according to the in-vention or partially premixed components, e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.
The compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
The compounds of the present invention are effective through both contact and ingestion.
Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
The compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g.
through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the present invention.
Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
As used herein, the term "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
The term "animal pest" includes arthropods, gastropods, and nematodes.
Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
The term "crop" refers to both, growing and harvested crops.
The term "plant" includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet;
fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, pumpkins, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco;
nuts, e.g. walnuts;
pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
carnation, petunias, geranium/pelargoniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane;
fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant" is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice. In plants, which have been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the genetic material of the plant. The one or more mutagenized or integrated genes are preferably selected from pat, epsps, cry1Ab, bar, cry1Fa2, cry1Ac, cry34Ab1, cry35AB1, cry3A, cryF, cry1F, mcry3a, cry2Ab2, cry3Bb1, cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asn1, and ppo5. The mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control. Of these properties, herbicide tolerance, e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance, is of particular importance. Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield oilseed rape being tolerant to imidazolinones, e.g. imazamox. Alternatively, genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady0 (glyphosate) and LibertyLinke (glufosinate).
Furthermore, insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins.
Genetically modified plants with insect resistance are commercially available under trade names including WideStrikee, Bollgarde, Agrisuree, Herculexe, YieldGardO, Genuity0, and Intactae.
Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits).
Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance. In general, all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http://www.isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CE RA)" (httplicera-gmc.org/GMCropDatabase).
It has surprisingly been found that the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
The term "plant propagation material" refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
The term "seed" embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to g per hectare, or 40 to 50 g per hectare.
The compounds of the present invention are particularly suitable for use in the treatment of seeds 40 in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
The present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the present invention. The protection of the seedling's roots and shoots is preferred.
.. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
The term "seed treatment" comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried .. out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
The present invention also comprises seeds coated with or containing the active compound. The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser .. part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, .. bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g.
tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF.
.. These formulations can be applied to the seed diluted or undiluted.
Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter.
Preferably, the formulations are applied such that germination is not included.
The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 %
by weight.
In a preferred embodiment a FS formulation is used for seed treatment.
Typically, a FS
formulation may comprise 1-800 g/I of active ingredient, 1-200 g/I Surfactant, 0 to 200 g/I
antifreezing agent, 0 to 400 g/I of binder, 0 to 200 g/I of a pigment and up to 1 liter of a solvent, preferably water.
Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/I) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/I) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
The invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
The compounds of the present invention may also be used for improving the health of a plant.
Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.
As used herein "an effective and non-phytotoxic amount" means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
The terms "plant" and "plant propagation material" are defined above.
"Plant health" is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person.
The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the present invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.
As used herein, the term "non-crop insect pest" refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish-or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (e.g.
http://www.pherobase.com), and are known to those skilled in the art.
For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
Formulations of the compounds of the present invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.
The oil spray formulations differ from the aerosol recipes in that no propellants are used.
For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
The compounds of the present invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the present invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
The compounds of the present invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc.
from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
Customary application rates in the protection of materials are, for example, from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2treated material, desirably from 0.1 g to 50 g per m2.
Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
The compounds of the the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
insects from the order of Lepidoptera, for example Achroia grisella, Aclerisspp. such as A.
fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp.
such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A.
exclamation/s, A.
fucosa, A. 1;osilon, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophlla pometaria, Ampelophaga rubtginosa, Amyelois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota sanatoria, Antheraea pemyi, Anticarsia (=Thermesia)spp. such as A. gemmatalis; Apamea spp., Aproaerema modicella, Archt;os spp. such as A. argyrosplla, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetis mindara, Austroasca .. viridtgn:sea, Autographa gamma, Autographa nign:signa, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblast49 cactorum, Cadra cautella, Calingo brazil/ens/s, Calopas theivora, Capua reticulana, Carposina spp. such as C.
Noonenst:9, C. sasakit,".
Cephus spp., Chaetocnema andula, Cheimatobia brumata, Ch/lo spp. such as C.
lndicus, C.
suppressaks, C. partellus; Choreutt:s pariana, Chon:stoneura spp. such as C.
conflictana, C.
fumiferana, C. longicellana, C. murinana, C. occeentaks, C. rosaceana;
Chrysodebc:s (=Pseudoplusia)spp. such as C. eriosoma, C. includens; Cirpht:s unt;ouncta, Clysia ambiguella, Cnaphalocerusspp., Cnaphalocroct:s medinaks, Cnephasia spp., Cochyks hospes, Coleophora spp., Col/as eurytheme, Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectaks, Cydia (=Carpocapsa)spp. such as C.
pomonella, C.
latiferreana; Dalaca noctudes, Datana integerrima, Dasychira pin/cola, Dendrolimusspp. such as D. pint, D. spectablgs, D. sibiricus; Desmia funeral/s, Diaphania spp. such as D. nit/dal/s, D.
hyalinata; Diatraea grandiosella, Diatraea saccharaks, aphthera festiva, Ear/as spp. such as E.
.. insulana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) cur/al/s, Elasmopalpus lignosellus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Ept;ohyas postvittana, Erannt:s ti/aria, Erionota thrax, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproct1:9 chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albllinea, Feltia spp. such as F.
subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G.
molesta, G. inopinata;
Halysidota spp., Harn:sina americana, Hedylepta spp., Helicoverpa spp. such as H. armigera (=Heliotht:s armigera), H. zea (=Heliotht:s zea); Heliotht:s spp. such as H.
assulta, H. sub flexa, H.
virescens; Hellula spp. such as H. undaks, H. rogataks; Helocoverpa gelotopoeon, Hemlleuca oliviae, Herpetogramma licarst:saks, Hibernia defoliaria, Hofmannophlla pseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoria flavolasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodes orbonalis, Leucoma sal/cis, Leucoptera spp. such as L. coffee//a, L. scitella; Leuminivora lycinivorella, Lithocolletis blancardella, Lithophane antennata, Llattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrott:s alb/costa, Loxostege spp. such as L. sticticaks, L. cereraks; Lymantria spp. such as L.
dt:spar, L. monacha;
Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. such as M.
americanum, M.
californicum, M. constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. contigurata;
Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulakS, Megalopyge lanata, Melanchra picta, Melanitt:s leda, Mods spp. such as M.
lapites, M. repanda; Mods lattpes, Monochroa fragariae, Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantak:s, Nepytia spp., Nymphula spp., aketicus spp., Om/odes indicata, Ompht:sa anastomosaks, Operophtera brumata, Orgyia pseudotsugata, Oriaspp., Orthaga thyn:sak:s, Ostrinia spp. such as 0. nubilaks; Oulema oryzae, Paleacrita vemata, Panok:s flammea, Pamara spp., Papaipema nebn:s, Papilio cresphontes, Paramyelds transitella, Paranthrene regaks, Paysandt:sia archon, Pectinophora spp. such as P. gossypiella; Peridroma saucia, Perileucoptera spp., such as P. coffee//a; Phalera bucephala, Phrygandia californica, Phthorimaea spp. such as P.
operculella; Phyllocnt:stt:s citrella, Phyllonorycterspp. such as P.
blancardella, P. crataegella, P.
1:ssikit, P. ringoniella; Pien:s spp. such as P. brassicae, P. rapae, P. nap/;
Pllocrods tnpunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusaks, P.
stultana; Platyptllia carduidactyla, Plebejus argus, Plodia interpunctella, Plusia spp, Plutella macukpenntS, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepgone, Pseudaletia spp. such as P. sequax, P. unipuncta; Pyrausta nubilaks, Rachtplusia nu, Richia alb/costa, Rhizobius ventraks, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festal/el/a, Scirpophaga spp. such as S. incertulas, S.
innotata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra sub flava, Sitotroga cerealella, Sparganotht:s plleriana, Spilonota lechriasp:s, S. ocellana, Spodoptera (=Lamphygma)spp. such as S.
cosmodes, S.
eridania, S. extgua, S. fruglperda, S. latt:sfascia, S. littoraltS, S. litura, S. omithogalli; Skgmellaspp., Stomopteryx subsecivella, Strymon bazochit, Sylepta derogata, Synanthedon spp.
such as S.
exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (=Cryptophlebia) leucotreta, Thaumetopoea piiyocampa, Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T cloacella, T
pellionella; Tineola Tortrixspp. such as T viridana; Trichophaga tapetzella, Trichoplusia spp. such as T ni;
Tuta (=Scrobtpalpula) absoluta, Udea spp. such as U rubtgak:s, U rubtgaks;
Virachola spp., Yponomeuta padella, and Zeiraphera canadenst:s;
insects from the order of Coleoptera, for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. plampenntS, A. sinuatus; Agriotes spp. such as A. fuscicolks, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstiliaks, Ant:sandrus dt:spar, An/sop//a austriaca, Anobium punctatum, Anomala corpulenta, Anomala rufocuprea, Anoplophoraspp. such as A. glabripennt:s; Anthonomusspp. such as A. eugenit; A.
grandt:s, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidaks, Atomaria spp. such as A. linean:s; Attagenus spp., Aulacophora femora//s, Blastophagus pimperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp.
such as B. lentis, B.
pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria flondensis, Callosobruchus chinensis, Cameraria ohndella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C. ass/mills, C. nap/; Chaetocnema tibia/is, Cleonus mendicus, Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Ctenicera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactyl/spa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D.
undecimpunctata, D.
speciosa, D. long/corn/s. D. semOunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa arnVera, Diloboderus abderus, Diocalandra frumenti (Diocalandra skgmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestt:s, E.
vtgintioctomaculata; Epitr&spp. such as E. hirkoennt:s, E. similan:s; Eutheola humiks, Eutinobothrus brasllienst:s, Faustinus cubae, Gibbium psyllodes, Gnathocerus comutus, Hellula undaks, Heteronychus arator, Hylamorpha elegans, Hylobius abiett:s, Hylotrupes bajulus, Hypera spp. such as H.
brunnelpenntS, H. post/ca;
Hypomeces squamosus, Hypothenemus spp., Ips typographus, Lachnostema consanguinea, Lasioderma serricome, Latheticus oryzae, Lathridius spp., Lema spp. such as L.
bllineata, L.
melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea, Limon/us californicus, LISsorhoptrus oryzophllus, LA-us spp., Luperodes spp., Lyctus spp. such as L.
bruneus; Liogenys fuscus, Macrodactylus spp. such as M. subspinosus; Maladera matrida, Megaplatypus mutates, Megasceks spp., Melanotus communt:s, Melt:gethesspp. such as M. aeneus;
Melolontha spp. such as M. Nopocastani, M. melolontha; Metamasius hemOterus, Microtheca spp., A/kgdo/us spp. such as M. fryanus, Monochamus spp. such as M. altematus; Naupactus xanthographus, NOtus hololeucus, Oberia brevis, Oemona hirta, ayctes rhinoceros, Oryzaephllus surinamenst:s, Oryzaphagus oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. such as P.
brassicae, P.
cochleariae; Phoracantha recurva, Phyllobius pyri, Phyllopertha hofficola, Phyllophaga spp. such as P. hellen,- Phyllotreta spp. such as P. chrysocephala, P. nemorum, P.
striolata, P. vittula;
Phyllopertha horticola, Popillia japonica, Premnotrypesspp., Psacothea hllan:s, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopettha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R.
palmarum, R. phoenict:s, R. vulneratus; Saperda candida, Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophllus spp. such as S. granaria, S. oryzae, S. zeamat:s;
Sphenophorus spp. such as S.
levt:s; Stegobium paniceum, Stemechus spp. such as S. subst:gnatus;
Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tnbolium spp.
such as T castaneum; Trogoderma spp., Tychius spp., Xylotrechusspp. such as X
pyrrhoderus;
and, Zabrus spp. such as Z tenebriodes;
insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. albopictus, A.
vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A.
gambiae, A. leucosphyrus, A. macultpenntS, A. minimus, A. quadrimaculatus, A.
sinenstS;
Bactrocera invadens, Bibio hortulanus, Calltphora erythrocephala, Calltphora vicina, Ceratitt:s capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. mace//aria;
Chrysops atlanticus, Chrysops discalis, Cho/sops sllacea, Cochliomyiaspp. such as C. hominivorax;
Contariniaspp.
such as C. sorghicola; Cordylobia anthropophaga, Culex spp. such as C.
nIgnpalpus, C. ppiens, C.
quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicodes furens, Culiseta inomata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. platura, D.
radicum; Dermatobia hominis, Drosophila spp. such as D. suzukit, Fannia spp. such as F.
canicularis; Gastraphllusspp.
such as G. intestinak:s; Geomyza tOunctata, Glossinaspp. such as G. fusapes, G. morsitans, G.
pa/pal/s. G. tachinodes; Haematobia irritans, Haplodiplost:s equestn:s, HOpelatesspp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppoboscaspp., Hydrellia phAopina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolit,-Luclliaspp. such as L. caprina, L.
cuprina, L. sericata; Lycoria pectoral/s. Mansonia tilt/Lanus, Mayetiola spp.
such as M. destructor;
Musca spp. such as M. autumnak:s, M. domestica; Muscina stabulans, Oestrus spp. such as 0.
ovt:s; Opomyza forum, Oscinellaspp. such as 0. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentOes, Phorbia spp. such as P. ant/qua, P. brassicae, P.
coarctata; Phytomyza gymnostoma, Pros/mu//urn mbdum, Ps/la rosae, Psorophora columbiae, Psorophora discolor, Rhagolett:sspp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R.
pomonella; Rivellia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidak:s; Simulium vittatum, Sitodiplost:s mosellana, Stomoxys spp. such as S. calcitrans; Tabanus spp. such as T
atratus, T bovinus, T
lineola, T simik:s; Tannia spp., Thecodtplost:s japonenstS, TOula oleracea, TOula paludosa, and Wohlfahrtiaspp;
insects from the order of Thysanoptera for example, Ballothrips biform4s, Dichromothnps corbetti, Dichromothnpsssp., Echinothnps americanus, Enneothnps flavens, Frankliniellaspp. such as F.
fusca, F occidental/s. F tritid- Heliothn;osspp., Hercinothnps femorakS, Kakothn;osspp., Microcephalothnps abdominak:s, Neohydatothnps samayunkur, Pezothnps kellyanus, RhOphorothnps cruentatus, Scirtothn;osspp. such as S. citri, S. dorsak:s, S.
perseae;
Stenchaetothnps spp, Taeniothnps cardamoni, Taeniothnps inconsequens, Thripsspp. such as T
imagines, T hawaiienst:s, T oryzae, T palmi, T parvt:spinus, T tabact,-insects from the order of Hemiptera for example, Acizzia jamatonica, Acrostemumspp. such as A.
hllare; Acyrthosipon spp. such as A. onobrycht:s, A. p:sum; Adelges laricis, Adelges tsugae, Adelphocon:sspp., such as A. rapidus, A. superbus; Aeneolamiaspp., Agonoscenaspp., Aulacon'hum solani, Aleurocanthus woglumi, Aleurodesspp., Aleurodicus disperses, Aleurolobus barodenst:s, Aleurothrbaisspp., Amrascaspp., Anasa tn:stt:s, Antestiopst:sspp., Anurapht:s cardut;
Aondiellaspp., AphanostIgma piri, Aphdula nasturtit; Aphis spp. such as A.
craccivora, A. fabae, A. forbest; A. gossypit, A. grossulariae, A. maidiradict:s, A. point; A.
sambuci, A. schneden; A.
spiraecola; Arboridia apicakS, Arilus critatus, Aspidiellaspp., Aspidiotusspp., Atanusspp., Aulacasp:s yasumatsui, Aulacorthum solani, Bactericera cockerelli (Paratrioza cockerelli), Bemt:sia spp. such as B. argentifolit, B. tabad (Aleurodes tabaci); BAssusspp. such as B. leucopterus;
Brachycaudusspp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola;
Brachycolusspp., Brachycoo/nella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C.
fulgurakS, C. pyricola .. (Psylla piri); Calk:gypona marginata, Calocon:sspp., Campylomma livida, Capitophorus horni, Cameocephala fulgida, Caveleriusspp., Ceraplastesspp., Ceratovacuna lantgera, Ceroplastes ceriferus, Cerost;oha gossypit, Chaetost;ohon fragaefoki, Chionaspis tegalenst:s, Chlorita onukit, Chromapht:s jug/and/cola, Chiysomphalus ficus, COadulina mbila, Cimexspp. such as C.
hemOterus, C. lectulanus; Coccomytllus halli, Coccus spp. such as C.
hesperdum, C.
pseudomagnollarum; Corythucha arcuata, Creontiades dllutus, Ciyptomyzus Chrysomphalus aondum, Cryptomyzus Ctenarytaina spatulata, Cyrtopeltt:s notatus, Dalbulusspp., Dasynus pOen:s, Dialeurodes spp. such as D. atrifoli4. Dalbulus maid/s, Diaphonna spp.
such as D.
spp. such as D. bromellae; Dichelops furcatus, Diconocon:s hewetti, Dora/is spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysapht:s spp. such as D.
plantaginea, D. pyri, D.
radicola; Dysaulacon'hum pseudosolant; Dysdercus spp. such as D. cingulatus, D. Intermedius;
Dysmicoccus spp., Edessa spp., Geocon:sspp., Empoasca spp. such as E. fabae, E. solana;
Epidiasp:s lepen4 Enosoma spp. such as E. lantgerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E. Integriceps; Eusceks bllobatus, Euscht:stus spp. such as E.
heros, E. impictiventn:s, E. servus; Forinia theae, Geococcus coffeae, Glycaspl:s brimblecombei, Halyomorpha spp. such as H. halys; Hellopeltt:s spp., Homa/odt:sca vitrOennt:s (=H. coagulata), Horcias nobllellus, Hyalopterus prunt; Hyperomyzus lactucae, Icerya spp. such as I. purchase; Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanodeus tloca:ssimus, Lepidosaphes spp. such as L.
ulmi; Leptocon:sa spp., Leptoglossus phyllopus, LI;oapht:s erysimi, Lygus spp.
such as L. hesperus, L. lineolan:s, L. pratenst:s; Maconellicoccus hirsutus, Marchalina he//en/ca, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M. euphorbiae; Macrosteles quadrifineatus, Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanapht:s pyrarius, Melanapht:s sacchari, Melanocalks (=Tinocalks) caryaefoliae, Metcafiella spp., Metopolophium dirhodum, Monellia costa/is, Monelliopst:s pecan/s. Myzocalk:s coryli, Murgantia spp., Myzus spp. such as M.
ascalonicus, M. cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia Neotoxoptera formosana, Neomegalotomus spp, Nephotett&spp. such as N. malayanus, N.
mgropictus, N.
parvus, N. virescens; Nezara spp. such as N. viridula; Nllaparvata lugens, Nysius huttoni, Oebalus spp. such as 0. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hyalinOenntS, Parabemt:sia myricae, Parlatoria spp., Parthenolecanium spp. such as P. corni, P. persicae;
PemphIgus spp. such as P. bursar/us, P. populivenae; Peregrinus maidt:s, Perkinsiella saccharicida, Phenacoccus spp. such as P. acen:s, P. gossypit,". Phloeomyzus passerinit;
Phorodon humuk Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guldinit,".
Pinnasp:s aspidt:strae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformt:s, Psallus seriatus, Pseudacysta persea, Pseudaulacasp:s pentagona, Pseudococcus spp.
such as P. comstock4. Psylla spp. such as P. malt; Pteromalus spp., Pulvinaria amygdali, Pyrilla spp., Quadraspidiotusspp., such as Q. perniciosus; Quesada gtgas, Rastrococcus spp., Reduvius sentgs, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalost;ohum spp.
such as R. pseudobrassicas, R. insertum, R. maidt:s, R. padt,". Sagatodes spp., Sahlbergella singular/s. Sat:ssetia spp., Sappapht:s ma/a, Sappapht:s mak; Scaptocon:s spp., Scaphodes titanus, Schizapht:s graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insulan:s, Sp:sst:stllus festinus (=Stictocephala festina), Stephanitt:s nashi, Stephanitt:s pyriodes, StephanittS takeyai, Tenalaphara malayenst:s, Tetraleurodes perseae, Therioapht:s maculate, Thyanta spp. such as T accerra, T
perditor; Tibraca spp., Tomaspisspp., Toxoptera spp. such as T aurantit,".
Trialeurodes spp. such as T abuttionea, T ricini, T vaporariorum; Triatomaspp., Triozaspp., Typhlocybaspp., Unaspis spp. such as U. citri, U yanonensis; and Viteus vitifoli Insects from the order Hymenoptera for example Acanthomyops interjectus, Athalia rosae, Atta spp. such as A. captguara, A. cephalotes, A. cephalotes, A. laevtgata, A.
robusta, A. sexdens, A.
texana, Bombusspp., Brachymyrmexspp., Camponotusspp. such as C. floridanus, C.
pennsylvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp, Crematogasterspp., Dasymutilla ocadentalis, aprion spp., Dolichovespula maculata, Dorymyrmexspp., Dryocosmus kunphllus, Formica spp., Hoplocampa spp. such as H. minuta, H. testudinea; Indomyrmex humllis, Lasius spp.
.. such as L. mger, Linepithema hunge, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina long/corn/s.
Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris;
Phekklespp. such as P.
megacephala; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes ruNginosa, Prenolepis impairs, Pseudomyrmex gracllis, Scheltpron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, Sinvicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphexspp., Tapinoma spp. such as T melanocephalum, T sessile; Tetramorium spp. such as T
caespitum, T
bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V squamosal;
Wasmannia auropunctata, Xylocopa sp;
Insects from the order Orthoptera for example Acheta domesticus, CallOtamus italicus, Chortoicetes terminifera, Ceuthophllusspp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllusspp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp. such as L. mt:gratoria, L. pardalina;
Melanoplus spp. such as M.
bivittatus, M. femurrubrum, M. mexicanus, M. sanguimpes, M. spretus;
Nomadacn:s septemfasciata, Oedaleus senegalenst:s, Scapten:scusspp., Scht:stocercaspp. such as S.
americana, S. gregaria, Stemopelmatusspp., Tachycines asynamorus, and Zonozerus variegatus;
Pests from the Class Arachnida for example Acari,e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A.
maculatum), Argas spp. such as A. persicu), Boophllusspp. such as B. annulatus, B. decoloratus, B. microplus, Dermacentorspp. such as D.stivarum, D. andersoni, D. variabiks, Hyalomma spp.
such as H.
truncatum, Ixodes spp. such as I. ricinus, I rubicundus, I scapulan:s, I
holocyclus, I pacificus, RhOicephalus sanguineus, Ornithodorus spp. such as 0. moubata, 0. hermsi, 0.
turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp.
such as P. ovt:s, RhOicephalusspp. such as R. sanguineus, R. appendiculatus, RhOicephalus evettsi, Rhizoglyphus spp., Sarcoptesspp. such asS. Scabiet, and Family Eriophyidae including Aceriaspp. such as A.
sheldoni, A. anthocoptes, Acallitusspp., Aculops spp. such as A. lycopersici, A. pelekassi, Aculus spp. such as A. schlechtendak. Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora;
Eriophytes nbt:s and Eriophyesspp. such as Eriophyes sheldoni, Family Tarsonemidae including Hemitarsonemusspp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp. Steneotarsonemus spinki, Family Tenuipalpidae including Brevipalpus spp.
such as B.
phoenicis, Family Tetranychidae including Eotetranychusspp., Eutetranychusspp., 014g0nychu5 spp., Petrobia latens, Tetranychus spp. such as T cinnabarinus, T evansi, I
kanzawat; T, pacificus, T phaseulus, T tetanus and T urticae, Bryobia praetiosa; Panonychus spp. such as P.
ulmi, P. citri, Metatetranychus spp. and Oligonychusspp. such as 0. pratensis, a perseae, Vasates lycopersici, Raoiella id/ca, FamilyCarpoglyphidae including Carpoglyphusspp.;
Penthaleidaespp. such as Halotydeus destructor Family Demodicidae with species such as Demodexspp.; Family Trombicidea including Trombiculaspp.; Family Macronyssidae including Omothonyssusspp.; Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae;
Family Acaridae including Acarus siro; Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles reclusa;
Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root-knot nematodes, Melodogynespp. such as M. hap/a, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H.
avenae, H.
glycines, H. schachtit; H. trifoli4- Seed gall nematodes, Anguinaspp.; Stem and foliar nematodes, Aphelenchodesspp. such as A. bessey4. Sting nematodes, Belonolaimusspp. such as B.
longicaudatus; Pine nematodes, Bursaphelenchusspp. such as B. lIgnicolus, B.
xylophllus; Ring nematodes, Criconemaspp., Criconemellaspp. such as C. xenoplaxand C. omata;
and, Criconemodesspp. such as Criconemodes informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchusspp. such as D. destructor, D. dOsact,".Awl nematodes, Dolichodorusspp.;
Spiral nematodes, Heliocotylenchus multicinctus; Sheath and sheathoid nematodes, Hemicycliophoraspp. and Hemicriconemodesspp.; Hirshmanniella spp.; Lance nematodes, Hoploaimusspp.; False rootknot nematodes, Nacobbusspp.; Needle nematodes, Longdorusspp.
such as L. elongatus; Lesion nematodes, Pratylenchusspp. such as P.
brachyurus, P. neglectus, P. penetrans, P. curvitatus, P. goodey4. Burrowing nematodes, Radopholusspp.
such as R. simllis;
Rhadopholusspp.; Rhodopholusspp.;Reniform nematodes, Rotylenchusspp. such as R.
robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T
obtusus, T primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tylenchorhynchus spp. such as T claytoni, T dub/us; Citrus nematodes, Tylenchulusspp. such as T
semtpenetrans;
Dagger nematodes, Nohinema spp.; and other plant parasitic nematode species;
Insects from the order Isoptera for example Calotermes Coptotermesspp. such as C.
formosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C.
brevis, C. cavifrons; Globitermes sulfureus, Heterotermes spp. such as H.
aureus, H. longiceps, H.
tenuis; Leucotermes tiewpes, Odontotermes spp., Incisitermes spp. such as I.
minor, I Snyder Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermesspp., Procornitermesspp., Zootermopsis spp.
such as Z
angusticollis, Z nevadensis, Reticulitermesspp. such as R. hesperus, R.
tibia/is, R. speratus, R.
tiewpes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natalensis, Insects from the order Blattaria for example Blattaspp. such as B. orientalis, B. lateralis; Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea, Penplanetaspp.
such as P. americana, P. australasiae, P. brunnea, P. fuligginosa, P.
japonica; Supella long/pa/pa, Parcoblatta pennsylvanica, Euiycotis tloridana, Pycnoscelus surinamensis, Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephaldes spp. such as C. felts, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes canis, Tunga penetrans, and Nosopsyllus fasciatus, Insects from the order Thysanura for example Lept:sma saccharina, Ctenolept:sma urbana, and Thermobia domestica, Pests from the class Chilopoda for example Geophllus spp., Scutigera spp. such as Scutigera coleoptrata;
Pests from the class Diplopoda for example Blaniulus guttulatus, Julusspp., Narceusspp., Pests from the class Symphyla for example Scutigerella immaculata, Insects from the order Dermaptera, for example Forticula auricularia, Insects from the order Collembola, for example Onychiurusspp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Ont:scus asellus, Porcellio scaber, Insects from the order Phthiraptera, for example Damaliniaspp., Pediculus spp.
such as Pediculus humanus capitt:s, Pediculus humanus corpon:s, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eulystemus, Haematopinus sut:s;
Linognathus spp. such as Linognathus Boy/cola bow:9, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp., Examples of further pest species which may be controlled by compounds of fomula (I) include:
from the Phylum Mollusca, class Bivalvia, for example, Dret:ssenaspp.; class Gastropoda, for example, Arlon spp., Biomphalariaspp., Bulinusspp., Derocerasspp., Galba spp., Lymnaeaspp., Oncomelania spp., Pomacea canaliclata, Succinea spp.,-from the class of the helminths, for example, Ancylostoma duodena/e, Ancylostoma ceylanicum, Acylostoma brazil/ens/s, Ancylostoma spp., Ascan:s lubricodes, Ascan:s spp., Brugia malayi, Brugia timon;
Bunostomum spp., Chabertia spp., Cionorcht:sspp., Cooperia spp., Dicrocoelium spp., Dictyocaulus fl/aria, aphyllobothrium latum, Dracunculus medinenst:s, Echinococcus granulosus, Echinococcus mu/t//ocular/s, Enterobius vermiculan:s, Faciola spp., Haemonchus spp. such as Haemonchus contortus;
Heterala:sspp., Hymenolept:s nana, Hyostrongulusspp., Loa Loa, Nematodirusspp., Oesophagostomum spp., Op:sthorcht:s spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Scht:stosomen spp., Strongylodes fuelleborni, Strongylodes stercora lis, Stronylodes spp., Taenia saginata, Taenia solium, Tr/chine/la spiraltS, Tr/chine/la nativa, Tr/chine/la britow;
Tr/chine/la nelsoni, Tr/chine/la pseudopsiraltS, Trichostrongulus spp., Trichun:s trichuria, Wuchereria bancroffil The compounds of the present invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the present invention also relates to the use of a compound of the present invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites.
Furthermore, the present invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the present invention.
The present invention also relates to the non-therapeutic use of compounds of the present invention for treating or protecting animals against infestation and infection by parasites. Moreover, the present invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the present invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the present invention.
The present invention also relates to the non-therapeutic use of compounds of the present invention for controlling or combating parasites. Moreover, the present invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
The compounds of the present invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).
Furthermore, the compounds of the present invention can be applied to any and all developmental stages.
The compounds of the present invention can be applied as such or in form of compositions comprising the compounds of the present invention.
The compounds of the present invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.
The compounds of the present invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the present invention can be systemically or non-systemically effective.
The application can be carried out prophylactically, therapeutically or non-therapeutically.
Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.
As used herein, the term "contacting" includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at its locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the present invention.
The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.
As used herein, the term "parasites" includes endo- and ectoparasites. In some embodiments of the present invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
The compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively:
fleas (Siphonaptera), e.g. Ctenocephaldes felts, Ctenocephaldes canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Penplaneta japonica, Penplaneta brunnea, Penplaneta fukgginosa, Penplaneta australasiae, and Blatta or/entails; flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles macukpennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minim us, Anopheles quadrimaculatus, Calkphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops sllacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicodes furens, Culex ppiens, Culex nIgnpalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inomata, Culiseta melanura, Dermatobia hominis, Fannia caniculan:s, Gasterophllus intestinakS, Glossina morsitans, Glossina palpakS, Glossina fusapes, Glossina tachinodes, Haematobia irritans, Haplodtplost:s equestn:s, Hip elates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucllia cuprina, Lucllia sericata, Lycoria pectoral/s. Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovt:s, Phlebotomus argenttpes, Psorophora columbiae, Psorophora discolor, Prosimulium mbdum, Sarcophaga haemorrhoidak:s, Sarcophaga sp., Simulium viltatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus simik:s; lice (Phthiraptera), e.g. Pediculus humanus capitt:s, Pediculus humanus corpon:s, Pthirus pubis, Haematopinus eurystemus, Haematopinus sutS, Linognathus vituli, Boy/cola bow:9, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapulan:s, Ixodes holocyclus, Ixodes pacificus, RhIphicephalus sanguineus, Dermacentor andersoni, Dermacentor variab&s, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacot and Dermanyssus gallinae;
Actinedida (Prostigmata) und Acaridida (Astigmata), e.g. Acarap:s spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Ustrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemdocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (Heteropterida): Cimex lectularius, Cimex hemtpterus, Reduvius seniltS, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus,-Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g.
Trimenopon spp., Menopon spp., Trinoton spp., Boy/cola spp., Wemeckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichun:s spp., Capillaria spp.;
Rhabditida, e.g. Rhabditt:s spp., Strongylodes spp., Helicephalobus spp.;
Strongylida, e.g.
Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp.
(Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, 011ulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Mueller/us capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricodes, Ascan:s suum, Ascaridia gal/t;
Parascan:s equorum, Enterobius vermiculan:s (Threadworm), Toxocara can/s, Toxascan:s leonine, Skrjabinema spp., and Oxyun:s equ4.Camallanida, e.g. Dracunculus medinenst:s (guinea worm);
Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, apetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g.
Faciola spp., Fasciolodes magna, Paragonimus spp., Dicrocoelium spp., Fasciolopst:s buski, Clonorcht:s sinenst:s, Scht:stosoma spp., Trichobilhozia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. aphyllobothrium spp., Tenia spp., Echinococcus spp., ay//d/um caninum, Multiceps spp., Hymenolept:s spp., Mesocestodes spp., Vampirolep:s spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolept:s spp..
As used herein, the term "animal" includes warm-blooded animals (including humans) and fish.
Preferred are mammals, such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
Particularly preferred are domestic animals, such as dogs or cats.
In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
Generally, it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals.
For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid preparations;
- Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, .. and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.
Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
Gels are applied to or spread on the skin or introduced into body cavities.
Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.
Emulsions can be administered orally, dermally or as injections. Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.
Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.
Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
Suitable auxiliaries for this purpose are known in the art.
The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the present invention.
Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
Topical application may be conducted with compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
Generally it is favorable to apply solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
Preparation examples:
With appropriate modification of the starting materials, the procedures as described in the preparation examples below were used to obtain further compounds of formula I.
The compounds obtained in this manner are listed in the table C that follows, together with physical data.
Compounds can be characterized e.g. by coupled High Performance Liquid Chromatography /
mass spectrometry (HPLC/MS), by 1H-NMR and/or by their melting points.
Analytical HPLC - Method : Agilent Eclipse Plus C18, 50 X 4,6 mm, ID 5pm;
Elution: A = 10 mM
Amm. Formate (0.1 % Formic Acid), B = Acetonitrile (0.1 % Formic Acid), Flow =
1.2 ml/min. at 30 C; Gradient := 10% B to 100% B ¨3 min, hold for 1 min, 1 min - 10% B. Run Time = 5.01 min.
1H-NMR: The signals are characterized by chemical shift (ppm, 8 [delta]) vs.
tetramethylsilane respectively, CDCI3 for 13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplet, q = quartet, t = triplet, d = doublet and s = singlet.
Abbreviations used are: d for day(s), h for hour(s), min for minute(s), r.t./room temperature for 20 -25 C, Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, Et0Ac for ethyl acetate, THF for tetrahydrofuran, and t-BuOH for tert-butanol.
Example1: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-34244-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2- enylidene]amino]thiourea (C-1) Step 1: 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a solution of 5-bromo-2-chloro-pyrimidine (0.1 g) in N,N-Dimethyl formamide (3 mL), was added Potassium carbonate (0.142 g), Copper (I) iodide (0.01 g), 8-hydroxy quinoline (0.08 g) and 4-(trifluoromethoxy) aniline (0.11 g). The mixture was heated at 95 C for 24 h. The mixture was diluted with water (15 mL) and extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the resulting residue was subjected to flash silica gel column chromatography using a gradient of Ethyl acetate and Heptane as eluent to afford the titled compound as a off-white solid (0.05 g). LC/MS:
Rt : 1.86 min; MS: m/z = 334 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 10.12 - 9.94 (m, 1H), 8.74 - 8.56 (m, 2H), 7.89 -7.72 (m, 2H), 7.38 -7.24 (m, 2H).
Step 2: (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal:
A solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.1 g) was taken up in 1,4-Dioxane (4 mL) and water (1 mL) and the mixture degassed with nitrogen for 15 min. [1,I-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.01 g), Cesium carbonate (0.2 g) and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethy1-1,3,2-dioxaborolane (0.11 g) were added and the mixture degassed with nitrogen for an additional 10 min. The mixture was heated at 95 C for 4 h and subsequently cooled to ambient temperature. A solution of Hydrochloric acid (1 N) was added and the mixture stirred for 30 min. The mixture was neutralized with solid Sodium bicarbonate and extracted with Ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and evaporated under reduced pressure and the residue obtained was purified by flash column chromatography eluting with a gradient of Ehyl acetate and Heptane to afford (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal as a solid (0.03 g). LC/MS: Rt :
1.65 min; MS: m/z = 324 (M+1)+; 1H NMR (300 MHz, Dmso-c) 6 10.33 (s, 1H), 9.54 (s, 1H), 8.80 (s, 2H), 8.01 -7.80 (m, 2H), 7.48 - 7.34 (m, 2H), 7.32 (s, 1H), 2.02 (s, 3H).
Step 3: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-34244-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2- enylidene]amino]thiourea A mixture of (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.130 g) in Ethanol (3 mL) was heated at 80 C for 3 h. The mixture was cooled to ambient temperature and the precipated solid was filtered and washed with cold Ethanol and n-pentane to afford the titled compound (0.2 g). LC/MS: Rt :
1.96 min; MS: m/z =
515 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.74 (s, 1H), 10.10 (s, 1H), 9.72 (s, 1H), 8.69 (s, 2H), 7.96 (s, 1H), 7.91 -7.88 (m, 2H), 7.36 - 7.19 (m, 6H), 6.69 (s, 1H), 3.14 -3.05 (m, 1H), 2.14 (s, 3H), 1.19 - 1.17 (m, 6H).
Example 2: Synthesis of 1-(2,6-dimethylpheny1)-3-[(E)-RE)-2-methyl-34244-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0-2):
A mixture of (E)-2-methyl-34244-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) and 1-amino-3-(2,6-dimethylphenyl)thiourea (0.12 g) in Ethanol (3 mL) was heated at 80 C for 3 h. The mixture was subsequently cooled to ambient temperature, the suspended solids filtered, washed sequentially with cold ethanol, pentane and dried to afford the title compound (0.2 g). LC/MS: Rt :
1.89 min; MS: m/z = 501 (M+1)+; 1H NMR (300 MHz, DMSO-a) 5 11.67 (s, 1H), 10.09 (s, 1H), 9.61 (s, 1H), 8.69 (s, 2H), 7.94 (s, 1H), 7.91 ¨ 7.80 (m, 2H), 7.42 ¨7.22 (m, 2H), 7.21 ¨7.02 (m, 3H), 6.67 (s, 1H), 2.21 (s, 3H), 2.18 (s, 6H).
Example 3: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-34244-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-3):
To a stirred solution of 1-(2-isopropylpheny1)-3-[(2-methyl-3[244-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.170 g) in Ethanol (3 mL) was added Sodium acetate (0.082 g) and Methyl bromoacetate (0.25 g). The mixture was stirred at room temperature for 30 h and subsequently diluted with water and extracted with Ethyl acetate. The organic extracts were separated, dried over anhydrous Sodium sulfate and evaporated under reduced pressure. The residue obtained was subjected to flash silica gel column chromatography eluting with a gradient of Ethylacetate-Heptane to afford the title compound as a solid (0.16 g).
LC/MS: Rt : 1.99 min; MS: m/z = 555 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 10.14 (s, 1H), 8.61 (s, 2H), 8.02 (s, 1H), 7.96 ¨ 7.78 (m, 2H), 7.57 ¨ 7.40 (m, 2H), 7.40 ¨ 7.27 (m, 3H), 7.27 ¨ 7.19 (m, 1H), 6.78 (s, 1H), 4.33 ¨ 3.99 (m, 2H), 2.85 ¨ 2.67 (m, 1H), 2.01 (s, 3H), 1.14 ¨ 1.12 (m, 6H).
Example 4: Synthesis of (2Z)-3-(2, 6-dimethylpheny1)-2-[(2-methyl-3[244-(trifluoromethoxy) anilino]pyrimidin-5-yl] prop-2-enylidene]hydrazono]thiazolidin-4-one (0-4):
A mixture of 1-(2,6-dimethylpheny1)-342-methyl-34244(trifluoromethoxy)anilino]
pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.19 g), Sodium acetate (0.094 g) and Methyl bromoacetate (0.29 g) in Ethanol (4 mL) was stirred at r.t. for 24 h. The mixture was subsequently diluted with water and extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the residue obtained was subjected to silica gel flash column chromatography, eluting with a gradient of Ethyl acetate-Heptane to obtain the title compound (0.170 g). LC/MS: Rt : 1.95 min; MS: m/z = 541 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 10.11 (s, 1H), 8.61 (s, 2H), 8.02 (s, 1H), 7.95 ¨ 7.75 (m, 2H), 7.38 ¨ 7.28 (m, 2H), 7.28 ¨ 7.24 (m, 1H), 7.24 ¨ 7.16 (m, 2H), 6.78 (s, 1H), 4.22 (s, 2H), 2.14 (s, 3H), 2.08 (s, 6H).
Example 5: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-5):
Step 1: 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a stirred solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.1 g) in N, N-Dimethylformamide (3 mL) at 0 C was added sodium hydride (0.01 g). Methyl iodide (0.064 g) was added and the mixture stirred at r.t. for 12 h. The mixture was diluted with saturated Ammonium chloride solution, extracted with Ethyl acetate, the organic extracts dried over anhydrous Sodium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.05 g). LC/MS: Rt : 2.262 min; MS: m/z = 348 (M+1)+; 1H NMR
(300 MHz, DMS0-G) 6 8.53 (s, 2H), 7.54 ¨ 7.43 (m, 2H), 7.43 ¨ 7.32 (m, 2H), 3.44 (s, 3H), 1.20 (d, J= 19.4 Hz, 2H).
Step 2: (E)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal:
A mixture of 5-bromo-N-methyl-N[4-(trifluoromethoxy)phenyl] pyrimidin-2-amine (0.5 g) in 1,4-Dioxane (8 mL) and water (2 mL) was degassed with nitrogen gas for 15 min.
[1,1'-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.055 g), Cesium carbonate (1 g) and 2-[(E)-3, 3-diethoxyprop-1-enyI]-4, 4, 5, 5-tetramethy1-1, 3, 2-dioxaborolane (0.7 g) were added and the mixture heated at 95 C for 3 h. The reaction mixture was cooled to ambient temperature, acidified with IN HCI solution and stirred at r.t. for 30 min. The mixture was neutralized with solid Sodium bicarbonate, extracted with ethyl acetate, the organic layers dried over Sodium sulfate and evaporated under reduced pressure. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to obtain the title compound as a solid (150 mg). LC/MS: Rt : 1.98 min; MS: m/z = 324.2 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 59.59 (d, J= 7.8 Hz, 1H), 8.79 (s, 2H), 7.59 (d, J= 16.0 Hz, 1H), 7.56 ¨7.48 (m, 2H), 7.42 (d, J=
8.6 Hz, 2H), 6.84 (dd, J= 16.0, 7.8 Hz, 1H), 3.53 (s, 3H).
Step 3: 1-(2-isopropylpheny1)-34[3424N-methyl-4-(trifluoromethoxy)anilino]
pyrimidin-5-yl]prop-2-enylidene]amino]thiourea:
A mixture of (E)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.09 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.058 g) in Ethanol (3 mL) was heated at 80 C for 2 h. The mixture was subsequently cooled to ambient temperature, the suspended solids filtered and washed with cold Ethanol to afford the title compound (0.08 g). LC/MS: Rt :
1.90 min; MS: m/z =
515 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 8.64 (s, 2H), 8.00 ¨ 7.87 (m, 1H), 7.57 ¨ 7.43 (m, 2H), 7.45 ¨ 7.35 (m, 2H), 7.35 ¨ 7.29 (m, 1H), 7.29¨ 7.22 (m, 1H), 7.22 ¨ 7.12 (m, 2H), 6.99 ¨ 6.82 (m, 2H), 3.50 (s, 3H), 3.15 ¨ 2.94 (m, 1H), 1.15 (d, J= 6.9 Hz, 6H).
Step 4: (2Z)-3-(2-isopropylpheny1)-24[3424N-methyl-4-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one:
A mixture of 1-(2-isopropylpheny1)-3-[(E)-RE)-3424N-methyl-4-(trifluoromethoxy)aniline ]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.08 g), Sodium acetate (0.039 g) and Methyl bromo acetate (0.120 g) in Ethanol (3 mL) was stirred at r.t. for 12 h. The reaction mixture was subsequently diluted with water and extracted with Ethyl acetate. The organic extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the residue obtained subjected to silica gel flash column chromatograph eluting with a gradient of Ethyl acetate ¨ Heptane to afford the title compound (0.04 g). LC/MS: Rt: 1.97 min; MS: m/z = 555 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 6 8.65 (s, 2H), 8.00 (d, J= 9.3 Hz, 1H), 7.55 ¨ 7.44 (m, 4H), 7.44 ¨
7.35 (m, 2H), 7.35 ¨
7.27(m, 1H), 7.26 ¨ 7.19 (m, 1H), 7.12 ¨ 6.99 (m, 1H), 6.99 ¨ 6.85 (m, 1H), 4.29 ¨ 3.99 (m, 2H), 3.50 (s, 3H), 2.82 ¨2.64 (m, 1H), 1.21 ¨ 1.00 (m, 6H).
Example 6: Synthesis of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoro methoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (C-6):
Step 1: (E)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal A mixture of 5-bromo-N-methyl-N[4-(trifluoromethoxy) phenyl] pyrimidin-2-amine (0.4 g) in 1,4 Dioxane (6 mL) and water (1.5 mL) was degassed with nitrogen gas for 15 min.
[1,1'-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) (0.042 g), Cesium carbonate (0.751 g) and 2-[(E)-3, 3-diethoxyprop-1-enyI]-4, 4,5, 5-tetramethy1-1, 3, 2-dioxaborolane (0.590 g) were added and the mixture heated at 95 C for 4 h. The reaction mixture was cooled to ambient temperature, acidified with IN HCI solution and stirred at r.t. for 30 min. The mixture was neutralized with solid Sodium bicarbonate, extracted with ethyl acetate, the organic layers dried over Sodium sulfate and evaporated under reduced pressure. The resulting residue was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to obtain the title compound as a solid (0.2 g). LC/MS: Rt : 2.15 min; MS: m/z = 338.2 (M+1)+; 1H NMR (300 MHz, DMSO-a) 5 9.51 (s, 1H), 8.71 (s, 2H), 7.60 -7.47 (m, 2H), 7.47 -7.37 (m, 2H), 7.33 (s, 1H), 3.54 (s, 3H), 1.97 (s, 3H).
Step 2: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea:
A mixture of (E)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl] prop-2-enal (0.83 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.51 g) in Ethanol (6 mL) was heated at 85 C
for 3 h. The mixture was cooled to ambient temperature and the precipitated solid was filtered and washed with cold ethanol and n-pentane and dried to afford the desired product (0.850 g). LC/MS:
Rt : 2.37 min; MS: m/z = 529.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.71 (s, 1H), 9.69 (s, 1H), 8.59(s, 2H), 7.94(s, 1H), 7.53 - 7.50 (m, 2H), 7.41 -7.38 (m, 2H), 7.35 - 7.15 (m, 4H), 6.64(s, 1H), 3.52 (s, 3H), 3.14 - 3.01 (m, 1H), 2.16 (s, 3H), 1.17 (d, J= 6.9 Hz, 6H).
Example 7: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (C-7):
1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino] pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.67 g) was taken up in Ethanol (15 mL).
Ethyl-2-bromo acetate (0.97 g) and Sodium acetate (0.31 g) added and the mixture stirred a r.t. for 24 h. The reaction mixture was diluted with water and extracted with Ethyl acetate, the organic extracts dired over anhydrous Sodium sulfate and evaporated under reduced pressure. The residue obtained was purified by silica gel flash column chromatography using a gradient of Ethyl acetate and Heptane to afford the desired product. (0.59 g). LC/MS: Rt : 2.49 min; MS: m/z = 569.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.51 (s, 2H), 7.99 (s, 1H), 7.62 - 7.47 (m, 3H), 7.44 (dd, J=
8.1, 1.5 Hz, 1H), 7.42 - 7.36 (m, 2H), 7.32 (ddd, J= 8.6, 6.8, 2.0 Hz, 1H), 7.23 (dd, J= 7.9, 1.3 Hz, 1H), 6.74 (s, 1H), 4.29 - 3.95 (m, 2H), 3.51 (s, 3H), 2.84 - 2.66 (m, 1H), 2.10 (s, 3H), 1.13 (t, J= 6.3 Hz, 6H).
Example 8: Synthesis of 1-[(E)-[(E)-345-(dimethylamino)-64N-methy1-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]amino]-3-(2-isopropylphenyl)thiourea (C-8):
Step 1: Synthesis of 5-bromo-3-nitro-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine To a solution of 5-bromo-2-chloro -3-nitro pyridine (12 g, 0.050 mol) in n-butanol (100 mL) were added Triethyl amine (6.13 g, 0.060 mol) and 4-Trifluoromethoxy aniline (10.74 g, 0.060 mol). The mixture was heated at 125 C for 2 h. The mixture was subsequently cooled to ambient temperature and the precipitated solids were filtered and dried under vacuum to obtain the desired product as a brown solid (12.1 g, 63.3 % yield. LC/MS: Rt : 1.938 min; MS: m/z = 378 (M+1)+; 1H
NMR (300 MHz, DMSO-d6); 5 8.69 (d, J = 2.3 Hz, OH), 8.60 (d, J = 2.3 Hz, OH), 7.71 (d, J = 9.0 Hz, 1H), 7.37 (d, J = 8.6 Hz, 1H).
Step 2 : Synthesis of 5-bromo-N2[4-(trifluoromethoxy)phenyl]pyridine-2,3-diamine To a stirred solution of 5-bromo-3-nitro-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine (1.33 g) in Ethyl acetate (15 mL) was added Tin chloride dihydrate (3.1 g) and the mixture was heated at 80 C for 2 h. The mixture was subsequently cooled to ambient temperature and Sodium bicarbonate solution was added and the resultant mixture was filtered through a Celite bed. The organic layer was separated, washed with saturated Sodium chloride solution and water and dried over anhydrous Sodium sulphate. The organic layer was then evaporated under reduced pressure to get the desired product as a light brown solid (0.63 g, 53 % yield). LC/MS: Rt :
1.723 min; MS: m/z =
348.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 5 8.08 (s, 1H), 7.68 (d, J = 9.0 Hz, 2H), 7.52 (d, J =
2.2 Hz, 1H), 7.24 (d, J = 8.6 Hz, 2H), 7.07 (d, J = 2.2 Hz, 1H), 5.45 (s, 2H).
Step 3: Synthesis of 5-bromo-N2,N3,N3-trimethyl-N244-(trifluoromethoxy)phenyl]pyridine-2,3-diamine To a solution of 5-bromo-N2[4-(trifluoromethoxy)phenyl]pyridine-2,3-diamine (3.8 g) in N, N-Dimethyl formamide (30 mL) was added Sodium hydride, 60% suspension in mineral oil, (1 g) at 0 C and stirred for 15 minutes. Methyl iodide (7 g) was added drop-wise.The mixture was stirred at ambient temperature for 12 h and subsequently a saturated solution of Ammonium chlorde was added and the mixture extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and evaporated under reduced pressure and the resultant solids subjected to flash column chromatography on Silica gel using a gradient of Ethyl acetate/Heptane as eluent to afford the desired product as a brown solid (1.33 g, 31%). LC/MS:
Rt : 2.441 min; MS:
m/z = 390.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 58.04 (d, J = 2.2 Hz, 1H), 7.51 (d, J = 2.2 Hz, 1H), 7.21 (d, J = 8.1 Hz, 1H), 6.84 (d, J = 9.1 Hz, 2H), 3.29 (s, 3H), 2.65 (s, 6H).
Step 4 : Synthesis of (E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enal A mixture of 5-bromo-N2,N3,N3-trimethyl-N244-(trifluoromethoxy)phenyl]pyridine-2,3-diamine (0.130 g) in 1,4 Dioxane (4 mL) and water (1 mL) was degassed with Nitrogen gas for 15 minutes.
[1,I-Bis(diphenylphosphino)ferrocene]palladium(11) dichloride (0.012 g), Cesium carbonate (0.217 g,) and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.171 g) were added and the mixture heated at 95 C for 4 h. IN Hydrochloric acid solution was subsequently added and the mixture was neutralized with solid Sodium bicarbonate and extracted with Ethyl acetate.The Ethyl acetate extracts were separated and filtered through Celite, dried over anhydrous Sodium sulphate and evaporated under reduced pressure. The residue obtained was subjected to Silica gel flash column chromatography using a gradient of Ethyl acetate/Heptane as eluent to afford the desired product as a pale yellow solid (0.090 g, 71 %, yield). LC/MS: Rt : 2.302 min; MS: m/z = 380.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 5 9.57 (s, 1H), 8.22 (d, J = 2.0 Hz, 1H), 7.69 - 7.39 (m, 2H), 7.29 - 7.10 (m, 2H), 6.91 (d, J = 9.1 Hz, 2H), 3.37 (s, 3H), 2.57 (s, 6H).
Step 5 : Synthesis of 1-[(E)-[(E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]amino]-3-(2-isopropylphenyhthiourea To a solution of (E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enal (0.420 g) in Ethanol (5 mL) was added 1-amino-3-(2-isopropyl phenyl)thiourea (0.231 g) and the mixture heated at 85 C for 2 h. The reaction mixture was cooled to ambient temperature and the resulting precipitate was filtered, washed with cold Ethanol and n-Pentane to get the desired product as yellow solid (0.5 g, 78.3 %, yield). LC/MS: Rt :
2.49 min; MS: m/z =
571.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 6 11.75 (s, 1H), 9.71 (s, 1H), 8.11 (d, J = 1.9 Hz, 1H), 7.98(d, J = 1.2 Hz, 1H), 7.44(d, J =2.0 Hz, 1H), 7.38 - 7.20 (m, 4H), 7.20 - 7.13 (m, 2H), 6.83(d, J = 9.3 Hz, 3H), 3.31 (s, 3H), 3.19 - 2.95 (m, 1H), 2.60(s, 6H), 2.29 -2.17 (m, 3H), 1.19 (d, J = 6.9 Hz, 6H).
Example 9: Synthesis of (2Z)-2-[(E)-[(E)-345-(dimethylamino)-64N-methyl-4-(trifluoromethoxy) anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]hydrazono]-3-(2-isopropylphenyhthiazolidin-4-one (C-9) To a stirred solution of 1-[(E)-[(E)-345-(dimethylamino)-64N-methy1-4-(trifluoromethoxy)anilino]-3-pyridy1]-2-methyl-prop-2-enylidene]amino]-3-(2-isopropylphenyhthiourea (0.370 g) in Ethanol (5 mL) was added Sodium acetate (0.160 g) and Methyl-2-bromo acetate (0.496 g). The mixture was stirred for 12 h, Water was added and the mixture was subsequently extracted with Ethyl acetate, the organic extracts dried over anhydrous Sodium sulfate and evaporated under reduced pressure.
The residue obtained was subjected to flash column chromatography using a gradient of Ethyl acetate/Heptane as eluent to obtain the desired product as a yellow solid (0.170 g, 42 %). LC/MS:
Rt : 2.550 min; MS: m/z = 611.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 58.04 (d, J
= 2.1 Hz, 2H), 7.59 - 7.41 (m, 2H), 7.39 - 7.27 (m, 2H), 7.24 (dd, J = 7.9, 1.3 Hz, 1H), 7.16 (d, J = 8.7 Hz, 2H), 6.91 (s, 1H), 6.83(d, J = 9.1 Hz, 2H), 4.56 - 3.86 (m, 2H), 3.33(s, 4H), 2.76 (dd, J = 13.4, 6.5 Hz, 1H), 2.58 (s, 6H), 2.17 (d, J = 1.2 Hz, 3H), 1.14 (t, J = 6.9 Hz, 6H).
Example 10: Synthesis of (2E)-2-[(Z)43-(2-isopropylpheny1)-4-oxo-thiazolidin-2-ylidene]hydrazono] -N-methyl-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0-10) Step 1: 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a stirred solution of 5-bromo-2-chloro-pyrimidine (0.1 g) in N,N-Dimethylformamide (3 mL) were added Potassium carbonate (0.142 g), Copper(I)iodide (0.01 g), 8-hydroxy quinoline (0.08 g) and 4-(trifluoromethoxy) aniline (0.11 g). The mixture was heated at 95 C for 24 h, cooled to ambient temperature, diluted with Water and extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel flash column chromatography using a gradient of Ethyl acetate and Heptane as eluent to afford the desired compound as yellow solid (0.05 g, 27 % yield).
LC/MS: Rt : 1.80 min; MS: m/z = 336 (M+1)+.
Step 2: 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (2.5 g) in N, N-Dimethylformamide (10 mL) at 0 C was added Sodium Hydride (60 % dispersion in mineral oil) (0.449g) portion wise. Methyl iodide (0.7 mL) was added and the mixture stirred at ambient temperature for 12 h. The mixture was poured into ice and the precipitated solids were filtered and dried to get the desired product (2.5 g, 96 %). LC/MS: Rt : 2.25 min; MS: m/z = 348.15 (M+1)+.
Step 3: N2,N5-dimethyl-N244-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine To a solution of 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.5 g) in N-Methyl Pyrrolidone (6 mL) in a sealed tube was added Cu (I) oxide (0.021g) and a 40 % solution of Methylamine in water (6 mL). The mixture was heated at 80 C fpr 12 h and water (20 mL) followed by Ethyl acetate (20 mL) were added. The mixture was filtered through a Celite bed, the organic layer separated, dried over anhydrous Sodium sulphate and evaporated to dryness under reduced pressure. The reside was purified by Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.3 g, 70%) as a beige solid. LC/MS: Rt : 1.88 min; MS: m/z = 288.3 (M-1); 1H NMR (300 MHz, DMSO-d6) 5 7.91 (s, 2H), 7.45 - 7.33 (m, 2H), 7.33 - 7.24 (m, 2H), 5.41 (q, J = 5.3 Hz, 1H), 3.42 (s, 3H), 2.67 (d, J =
5.3 Hz, 3H).
Step 4: (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]acetic acid To a solution of 1-amino-3-(2-isopropylphenyl)thiourea (1 g) in Methanol (20 mL) was added Glyoxylic acid monohydrate (0.44 g) and the mixture stirred at ambient temperature for 2 h. The mixture was evaporated under reduced pressure and the residue was washed with n-Pentane to get the desired product (1.2g, 95 %) as a off white solid. LC/MS: Rt: 1.439 min; MS: m/z = 264 (M-1); 1H NMR (300 MHz, DMSO-d6) 5 12.34 (s, 1H), 10.32 (s, 1H), 7.44 - 7.37 (m, 2H), 7.33 (td, J =
7.8, 7.4, 1.7 Hz, 1H), 7.24 (td, J = 7.4, 1.8 Hz, 1H), 7.17 (dd, J = 7.8, 1.6 Hz, 1H), 3.05 (p, J = 6.9 .. Hz, 1H), 1.17 (d, J = 6.9 Hz, 6H).
Step 5: (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N-methyl-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide To a solution of N2,N5-dimethyl-N244-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine (0.2 g, 0.67 mmol) and (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]acetic acid (0.196 g) in Dichloromethane (20 mL) was added Diisopropylethylamine (0.25 mL) and a 50 %
solution of Propylphosphonic anhydride in Ethyl acetate (0.835g). The mixture was stirred for 12 h and subsequently poured into Water (30 mL) and extracted with Ethyl acetate (2 X
20 mL). The organic extracts were dried over anhydrous Sodium suphate and evaporated under reduced pressure and the residue obtained was subjected to Silica gel flash column chromatorgraphy eluting with a gradient of Ethyl acetate and Heptane to get the desired product ans a yellow solid (0.32 g, 87 %
yield). LC/MS: Rt: 1.178 min; MS: m/z = 546 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.77(s, 1H), 9.43 (s, 1H), 8.48 (s, 2H), 7.60 (s, 1H), 7.48 -7.27 (m, 8H), 7.27 - 7.07 (m, 4H), 3.45 (s, 5H), 3.24 (s, 5H), 2.58 - 2.50 (m, 120H), 1.13 (t, J = 6.1 Hz, 11H).
Step 6: (2E)-2-[(Z)43-(2-isopropylpheny1)-4-oxo-thiazolidin-2-ylidene]hydrazonoFN-methyl-N42-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide A mixture of (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N-methyl-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0.15 g), Sodium acetate (0.26 g, 2.75 mmol) and Methyl bromoacetate (0.11 mL) in Ethanol (20 mL) was stirred at 40 C for 12 h. The mixture was cooled to ambient temperature and Water (50 mL) was added and the mixture extracted with Ethyl acetate (2 X 50 mL). The combined organic extracts were dried over anhydrous Sodium sulphate and evaporated invacuo to a residue which was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.1 g, 62 %). LC/MS: Rt: 2.10 min; MS: m/z = 586.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.34 (s, 2H), 7.66 -7.09 (m, 9H), 4.40 -4.00 (m, 2H), 3.47 (s, 4H), 2.62 (d, J =
6.9 Hz, 1H), 1.03 (dd, J
.. = 22.9, 6.8 Hz, 6H).
Example 11: Synthesis of (2E)-2-[(Z)43-(2-isopropylpheny1)-4-oxo-thiazolidin-2-ylidene]hydrazonoFN424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (C-11) A mixture of (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0.1 g, 0.188 mmol), Sodium acetate (0.154 g) and Methyl bromoacetate (0.076 mL) was taken up in Ethanol (20 mL) and stirred at 40 C for 12 h.
The mixture was cooled to ambient temperature and Water (50 mL) was added and extracted with Ethyl acetate ( 2 X 50 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the resultant residue was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the desired product (0.05 g, 46%). LC/MS: Rt: 2.149 min; MS: m/z = 572.3 (M+1)+;
1H NMR (300 MHz, DMSO-d6) 5 10.36 (s, 1H), 8.66 (s, 2H), 7.67 (s, 1H), 7.49 (d, J = 9.0 Hz, 3H), 7.37 (d, J = 8.4 Hz, 3H), 7.26 (dd, J = 7.9, 1.4 Hz, 1H), 4.51 -3.98 (m, 2H), 3.48 (s, 3H), 1.13 (dd, J = 6.9, 4.4 Hz, 6H).
Example 12: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-346-[N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-12) Step 1: Synthesis of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine A mixture of 2-amino-5-bromo pyridine (4.4 g), Copper (II) acetate (10.85 g) and Potassium phosphate (6.128 g) in Dimethylsulfoxide (70 mL) was heated at 100 C for 24 h. The mixture was subsequently cooled to ambient temperature, Ethyl acetate was added and the mixture filtered through Celite. The organic layer was separated, washed with saturated Sodium chloride solution, Water and subsequently dried over anhydrous Sodium sulphate. The organic layer was then evaporated invacuo and the residue subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to afford the desired product as a brown solid. (2.3 g, 27 %). LC/MS: Rt : 2.139 min; MS: m/z = 335.30 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.29 (d, J = 2.5 Hz, 1H), 7.79 (d, J = 9.1 Hz, 2H), 7.48 - 7.14 (m, 2H), 6.88 (dd, J =
8.9, 1.4 Hz, 2H).
Step 2: Synthesis of 5-bromo-N-methyl-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine To a 0 C solution of 5-bromo-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine (2.3 g) in N, N-Dimethyl formamide (15 mL) was added Sodium hydride (0.2 g). Methyl iodide (1.47 g) was added drop-wise and the mixture stirred at ambient temperature for 12 h. Saturated Ammonium chloride solution was added and the mixture extracted with Ethyl acetate and the extract was dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of Ethyl acetate and heptane to get the desired product as a off-white solid (1.75 g, 73 %). LC/MS: Rt: 2.209 min;
MS: m/z = 349.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 58.23 (d, J = 2.5 Hz, 1H), 7.65 (dt, J =
9.1, 2.0 Hz, 1H), 7.43 (s, 4H), 6.58 (d, J = 9.1 Hz, 1H), 3.37 (s, 3H).
Step 3: Synthesis of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal A mixture of 5-bromo-N-methyl-N[4-(trifluoromethoxy)phenyl]pyridin-2-amine (1.75 g, 5.05 mmol), 1,4 Dioxane (20 mL) and Water (5 mL) was degassed with nitrogen gas. [1,1'-Bis(diphenyl phosphino)ferrocene]palladium(II) dichloride (0.370 g), Cesium carbonate (3.3 g) and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethy1-1,3,2-dioxaborolane (2.59 g) were added and the degassing continued for a further 10 min. The mixture was heated at 90 C
for 3 h and cooled to ambient temperature. 1N Hydrochloric acid solution was added and the mixture was neutralized with solid Sodium bicarbonate. The mixture was extracted with Ethyl acetate and the extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the resultant residue was subjected to Silica gel flash chromatography eluting with a Ethyl acetate/Heptane gradient to get the desired compound as a white solid solid (1.2 g, 71 %). LC/MS: Rt : 2.170 min; MS: m/z = 337.2 (M+1); 1H NMR (300 MHz, DMSO-d6) 5 9.49 (s, 1H), 8.47 (d, J = 2.4 Hz, 1H), 7.84 (dd, J = 9.1, 2.5 Hz, 1H), 7.61 ¨7.41 (m, 4H), 7.37 (s,1H), 6.66 (d, J = 9.0 Hz, 1H), 3.47 (s, 3H), 1.97 (d, J = 1.1 Hz, 3H).
Step 4: Synthesis of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]-3-pyridyl]prop-2-enylidene]amino]thiourea To a stirred solution of (E)-2-methy1-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal (0.350 g) in Ethanol (4 mL) was added 1-amino-3-(2-isopropylphenyl)thiourea (0.217 g) and the mixture heated at 85 C for 3 h. Water was added and the mixture was extracted with ethyl acetate, the extracts dried over anhydrous Sodium sulphate, evaporated and the residue was flash chromatographed over Silica gel to get the desired product as a yellow solid (0.22 g, 40 %). LC/MS:
Rt : 2.423 min; MS: m/z = 528.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.68 (s, 1H), 9.66 (s, 1H), 8.37 ¨ 8.25 (m, 1H), 7.94 (s, 1H), 7.77 ¨7.62 (m, 1H), 7.52 ¨ 7.38 (m, 5H), 7.44 ¨ 7.26 (m, 2H), 7.27(s, 1H), 7.26 ¨ 7.10 (m, 1H), 6.72 ¨ 6.61 (m, 2H), 4.03(q, J = 7.1 Hz, 1H), 3.44(s, 4H), 3.09 (p, J = 6.8 Hz, 1H), 2.16 (s, 3H), 1.99 (s, 1H), 1.18 (d, J = 6.9 Hz, 6H).
Step 5: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enylidene]hydrazono]thiazolidin-4-one To a stirred solution of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]-3-pyridyl]prop-2-enylidene]amino]thiourea (0.175 g) in Ethanol ( 4 mL) were added sodium acetate (0.082 g), and Methyl-2-bromo acetate (0.25 g) and the mixture stirred for 16 h. The mixture was subsequently diluted with Water and extracted with Ethyl acetate, the extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure to get a residue which was flash chromatographed to ger the desired product as yellow solid (0.08 g, 40 %, yield). LC/MS: Rt : 2.465 min; MS: m/z = 568.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 8.26 (d, J = 2.3 Hz, 1H), 7.99 (s, 1H), 7.64 (dd, J = 9.0, 2.4 Hz, 1H), 7.55 ¨
7.38 (m, 6H), 7.32 (ddd, J = 8.6, 6.8, 2.0 Hz, 1H), 7.23 (dd, J = 7.9, 1.4 Hz, 1H), 6.80 (s, 1H), 6.64 (d, J = 8.9 Hz, 1H), 4.20 (d, J = 17.4 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.43 (s, 3H), 2.76 (p, J =
6.6 Hz, 1H), 2.14 ¨ 2.07 (m, 3H), 1.13 (t, J = 6.4 Hz, 6H).
Example 13: Synthesis of (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]acetamide (0-13) Step 1: N2-methyl-N2[4-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine To a solution of 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (1g) in N-Methylpyrrolidone (10 mL) in a sealed tube was added Copper (1) oxide (0.041 g) and a 30 %
solution of Methyl amine in water (10 mL). The mixture was heated at 80 C for 12 h. Water (20 mL) and Ethyl acetate (20 mL) were added and the mixture filtered through Celite.
The organic layer was separated, washed with a saturated solution of Sodium chloride, dried over anhydrous Sodium sulphate and evaporated invacuo. The residue obtained was subjected to Silica gel flash column chromatography using a Ethyl acetate/Heptane gradient to obtain the desired product (0.7 g, 85 %) as a beige solid. LC/MS: Rt: 1.715 min; MS: m/z = 285.2 (M-1).
Step-2: (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]-N424N-methyl-4-(trifluoromethoxy) anilino]pyrimidin-5-yl]acetamide To a solution of N2-methyl-N2[4-(trifluoromethoxy)phenyl]pyrimidine-2,5-diamine (0.1 g) and (2E)-2-[(2-isopropylphenyhcarbamothioylhydrazono]acetic acid (0.10 g) in Dichloromethane (10 mL) was added Diisopropylethylamine (0.125 mL) and a 50 % solution of Propylphosphonic anhydride solution (0.45 g). The mixture was stirred at ambient temperature for 12 h. Water (30 mL) was added and the mixture extracted with Ethyl acetate (2 X 20 mL). The organic extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the resultant residue was subjected to Silica gel flash column chromatography to get the desired product (0.32g, 87 %) as a yellow solid. LC/MS: Rt : 2.134 min; MS: m/z = 532 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 5 12.29 (s, 1H), 10.36 (s, 1H), 10.13 (s, 1H), 8.55 (s, 2H), 7.56 - 7.45 (m, 3H), 7.45 - 7.34 (m, 4H), 7.26 (dtd, J = 22.5, 8.5, 7.8, 1.7 Hz, 2H), 3.48 (s, 3H), 3.07 (p, J =
6.8 Hz, 1H), 1.19 (d, J = 6.9 Hz, 6H).
Example 14: Synthesis of 1-(2-isopropylpheny1)-3-[(E)(E)-3424N-methyl-4-(trifluoromethoxy) anilino]pyrimidin-5-yl]prop-2-enylidene]amino]imidazolidine-2,4-dione (0-14) A mixture of (E)-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.135 g), 3-amino-1-(2-isopropylphenyl)imidazolidine-2,4-dione (0.097g) and Concentrated Hydrochloric acid .. (2 drops) in Ethanol was heated at 80 C for 3 h. The mixture was cooled to ambient temperature and the precipitated solids were filtered and washed with cold ethanol and dried under vacuum to afford the desired product as a beige colored solid. (0.064 g, 28%). LC/MS: Rt : 2.180 min; MS: m/z = 539 (M+1)+.
Example 15: Synthesis of 1-(2-isopropylpheny1)-3-[(E)-[(E)-2-methy1-3-[6-[N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enylidene]amino]thiourea (C-15) A mixture of (E)-2-methy1-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal (0.32 g) and 1-amino-3-(2-isopropylphenyl)thiourea ( 0.217 g) in Ethanol (5 mL) was heated at 85 C for 3 h. The mixture was cooled to ambient temperature, diluted with water, extracted with Ethyl acetate and the extracts were dried over anhydrous Sodium sulphate and evaporated invacuo. The residue obtained was subjected to flash column chromatography using a gradient of Ethyl acetate and heptane as eluent to afford the desired product as a yellow solid (0.26 g, 46 %). LC/MS: Rt:
2.39 min; MS: m/z = 528.7 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 11.70 (s, 1H), 9.68 (s, 1H), 8.31 (d, J = 2.3 Hz, 2H), 7.94 (s, 1H), 7.81 (dd, J = 9.2, 2.4 Hz, 2H), 7.59 -7.14 (m, 12H), 6.72 (d, J
= 8.5 Hz, 3H), 3.09 (p, J = 6.8 Hz, 1H), 2.16 (s, 3H), 1.18 (d, J = 6.8 Hz, 7H).
Example 16: Synthesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-344-methyl-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0-16) Step 1: 5-bromo-2-chloro-4-methyl-pyrimidine A mixture of 5-Bromo 2,4-dichloropyrimidine (0.4 g) and Iron(111)acetylacetonate (0.062 g) in Tetrahydrofuran (10 mL) was cooled to 0 C. Methyl magnessium bromide (3 M
solution in Diethyl ether) (0.76 mL) was added dropwise and the mixture stirred for 2 h. Saturated Ammonium Chloride solution was added and the mixture extracted with Ethyl acetate (2 X
20 mL). The organic extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure to get a residue which was purified by Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and n-heptane to afford the desired product (0.220 g, 60 %) as a white solid. 1H
NMR (300 MHz, 0D0I3) 5 8.52 (s, 1H), 2.57 (s, 3H).
Step 2: 5-bromo-4-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine A mixture of 5-bromo-2-chloro-4-methyl-pyrimidine (2 g), 4-Trifluoromethoxyaniline (2.04 g), concentrated Hydrochloric acid solution (0.2 mL) in in 2-propanol (20 mL) was heated at 100 C for 4 h. The mixture was subsequently cooled to room temperature, poured into ice and basified with a saturated solution Sodium bicarbonate solution and precipitated solids were filtered. The filtered solid was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and n-Heptane to afford the desired product (1.75 g, 52 %) as an off-white solid. LC/MS:
Rt: 2.20 min; MS: m/z = 346.1 (M-1); 1H NMR (300 MHz, 0D0I3) 5 8.32 (s, 1H), 7.88 (s, 1H), 7.63 -7.51 (m, 2H), 7.19 -7.07 (m, 2H), 2.50 (s, 3H).
Step 3: 5-bromo-N,4-dimethyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To the solution of 5-bromo-4-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (1.5 g) in N, N-Dimethylformamide (30 mL) at 0 C was added Sodium hydride (60% dispersion in mineral oil) (0.207g) portion wise. Methyl iodide (0.35 mL) was added and the mixture stirred at 0 C for 1 h.
The reaction mixture was poured into ice and extracted with Ethyl acetate (2 X
20 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the residue subjected to Silica gel flash column chromatography using a gradient of Ethyl acetate and n-heptane as eluent to get the desired product to get the desired product (1.4 g, 89 % yield) as a beige solid. LC/MS: Rt : 2.388 min; MS: m/z = 364.3 (M+1)+;
1H NMR (300 MHz, 0D0I3) 5 8.20 (s, 1H), 7.27 (d, J = 9.0 Hz, 2H), 7.17 (d, J = 8.1 Hz, 2H), 3.47 (d, J = 1.3 Hz, 3H), 2.40 (d, J = 7.0 Hz, 3H).
Step 4: (E)-2-methy1-344-methy1-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal A mixture of 5-bromo-N,4-dimethyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.25 g), Cesium carbonate (0.45 g) and 2-[(Z)-3,3-diethoxy-1-methyl-prop-1-eny1]-4,4,5,5-tetramethy1-1,3,2-dioxaborolane (0.28 g) in 1,4-Dioxane (12 mL) and water (3 mL) was degassed for 10 min, followed by the addition of [1,I-Bis(diphenylphosphino)ferrocene] palladium(II) dichloride (0.05 g) and the mixture heated at 90 C for 2 h. The mixture was subsequently cooled to ambient temperature and water (10 mL) was added and the mixture extracted with Ethyl acetate (20 mL).
The Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the residue obtained was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate/n-Heptane to afford the desired product (0.2 4g, 99 %) as an off white solid. Rt :2.173 min; MS: m/z = 352.4 (M+1)+; 1H NMR (300 MHz, 0D013) 5 9.52 (s, 1H), 8.33 (s, 1H), 7.29 (d, 2H), 7.17 (d, 2H), 3.52 (s, 3H), 2.39 (s, 3H).
Step 5: 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-344-methyl-24N-methy1-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]prop-2-enylidene]amino]thiourea A mixture of (E)-2-methy1-344-methy1-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.12 g) in Ethanol (10 mL) was heated at 80 C for 2 h. The mixture was cooled to ambient temperature and the precipitated solids were collected by filtration, washed with cold Ethanol and dried under vacuum to afford the title compound 0.2 g (65 %) as a yellow solid. LC/MS: Rt : 2.411min; MS: m/z = 541.7 (M)-; 1H NMR
(DMSO-d6): 5 11.71 (s, 1H), 9.67 (s, 1H), 8.32 (s, 1H), 7.98 (s, 1H), 7.56 -7.46 (m, 2H), 7.43 -7.30 (m, 3H), 7.30 -7.14 (m, 3H), 6.74 (s, 1H), 3.51 (s, 3H), 3.08 (p, J = 6.9 Hz, 2H), 2.34 (s, 3H), 2.06 - 1.98 (m, 3H), 1.18 (d, J = 6.9 Hz, 6H).
Example 17: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-344-methyl-24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-17) A mixture of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-344-methyl-24N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]prop-2-enylidene]amino]thiourea (0.1g), Sodium acetate (0.091 g), Methyl bromoacetate (0.075 mL) was taken up in Ethanol (20 mL) and the mixture stirred at 40 C for 12 h. The mixture was diluted with water (50 mL) at ambient temperature and extracted with Ethyl acetate (2 X 50 mL). The combined organic layers were dried over anhydrous Sodium suphate and evaporated invacuo and the residue obtained was subjected to Silica gel Flash column chromatography using a gradient of Ethylacetate/Heptane to afford the title compound (0.08 g, 75 %) as a yellow solid. LC/MS: Rt: 2.498 min; MS: m/z = 583.4 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 5 8.33 (s, 1H), 8.10 (s, 1H), 7.55 - 7.46 (m, 4H), 7.41 (dd, J = 19.5, 8.0 Hz, 3H), 7.36 - 7.19 (m, 2H), 6.91 (s, 1H), 4.28 - 4.03 (m, 2H), 3.50(s, 3H), 2.28 (s, 3H), 1.98(d, J =
1.2 Hz, 3H), 1.19 -1.08 (m, 6H).
Example 18: Synthesis of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylideneamino]thiourea (0-18) Step 1: 24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-ol A mixture of 5-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (1.8 g) and Triisopropylborate (1.82 mL) was taken up in Tetrahydrofuran (30 mL) and cooled to -78 C. A
solution of n-BuLi (1.6 M in n-hexane, 4.827mL) was added and the mixture allowed to warm upto -20 C for 20 min. Acetic acid (1.5 mL) followed by Methanol (8 mL) was added and the mixture evaporated under reduced pressure. To the resultant residue, Methanol (2 mL), Water (12 mL) and a solution of Hydrogen Peroxide (20 % in water, 1.5 mL, 10.34 mmol) was added and the mixture stirred at ambient temperature for 12 h. The mixture was subsequently diluted with water (50 mL) and extracted with Ethyl acetate ( 2 X 50 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated invacuo and the resultant solid was purified by Silica gel flash column chromatography with a gradient of Ethyl acetate/Heptane as eluent to afford the desired product (1 g, 68%yield) as a white solid. LC/MS: Rt: 1.788 min; MS:
m/z = 286.3 (M+1)+;
1H NMR (300 MHz, DMSO-d6) 5 9.47 (s, 1H), 8.05 (s, 2H), 7.48 -7.37 (m, 2H), 7.32 (d, J = 8.6 Hz, 2H), 3.43 (s, 3H).
Step 2: 5-(2,2-diethoxyethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine To a solution of 24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-ol (0.25 g) in N,N-Dimethylacetamide (2 mL), was added KOH (0.098 g) followed by Bromoacetaldehyde diethylacetal (0.2 mL). The mixture was heated to 100 C for 2 h and subsequently cooled to room temperature. The mixture was diluted with water (20 mL) and extracted with Ethyl acetate Et0Ac (2 X 20 mL). The combined organic extracts were washed with a saturated solution of Sodium chloride, dried over anhydrous Sodium sulphate and evaporated under reduced pressure to afford the title ocmpoun as a pale yellow oil (0.25g, 71 %) . LC/MS: Rt : 2.23 min;
MS: m/z = 402.9 (M+1)+; 1H NMR (300 MHz, 0D0I3) 58.10 (s, 1H), 7.32 ¨ 7.21 (m, 1H), 7.16 (d, J
= 8.5 Hz, 3H), 4.72 (t, J = 5.1 Hz, 1H), 3.91 (d, J = 5.1 Hz, 1H), 3.77 ¨3.63 (m, 2H), 3.63 ¨3.48 (m, 3H), 3.46 (s, 2H), 3.30 (d, J = 5.5 Hz, 1H), 1.17 (td, J = 7.1, 1.8 Hz, 6H).
Step 3: 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyacetaldehyde To a solution of 5-(2,2-diethoxyethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.2 g) in Acetone (4 mL) was added a solution of Hydrochloric acid (1 N, 1 ml) and the mixture heated at 70 C for 5 h. The reaction was diluted with water (4 mL) and extracted with Ethyl acetate (2 X 10 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the resultant residue was subjected to flash column chromatography using a gradient of Ethyl acetate/Heptane to afford the title compound as a colorless oil (0.14 g, 86%). LC/MS: Rt : 1.612 min; MS: m/z = 327 (M+1)+; 1H
NMR (300 MHz, 0D0I3) 59.85 (s, 1H), 8.17 (s, 2H), 7.36 (d, J = 9.0 Hz, 2H), 7.25 (d, J = 8.4 Hz, 2H), 4.61 (s, 2H), 3.54 (s,3H).
Step 4: 1-(2-isopropylpheny1)-3-[(E)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylideneamino]thiourea A mixture of 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyacetaldehyde (0.15 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.10 g) in Ethanol ( 5 mL) was heated at 80 C for 1 h.
Subsequently, the mixture was evaporated under reduced pressure to get the title compound as a white solid (0.16 g, 67 %). LC/MS: Rt : 2.187 min; MS: m/z = 519.65 (M+1)+; 1H
NMR (300 MHz, DMSO-d6) 6 11.73 (s, 1H), 9.82 (s, 1H), 8.34 (s, 2H), 7.57 (t, J = 5.2 Hz, 1H), 7.51 ¨ 7.39 (m, 2H), 7.36 (s, 2H), 7.30 (dd, J = 11.3, 5.3 Hz, 2H), 7.27 ¨ 7.11 (m, 3H), 4.77 (d, J
= 5.2 Hz, 2H), 3.45 (s, 3H), 3.02 (p, J = 6.9 Hz, 2H), 1.12 (d, J = 6.9 Hz, 6H).
Example 19: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylidenehydrazono]thiazolidin-4-one (0-19) A mixture of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxyethylideneamino]thiourea (0.1 g), Sodium acetate (0.095 g), Methyl bromoacetate (0.078 mL) in Ethanol (20 mL) was stirred at 40 C for 12 h. The mixture was subsequently diluted with Water (50 mL) and extracted with Ethyl acetate (2 X 20 mL). The combined extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was purified by Silica gel flash column chromatography using a gradient of Ethyl acetate and heptane as eluent to afford the title compound (0.06 g, 56 %) as a white solid. LC/MS: Rt: 2.25 min; MS: m/z = 559.3 (M+1)+. 1H NMR (300 MHz, DMSO-d6) 6 8.256 (s, 2H), 7.672 (m, 1H), 7.431-7.462 (m, 4H), 7.327 ¨7.356 (m, 3H), 7.195 ¨ 7.251 (m, 1H), 4.79 (d, J= 4.5Hz, 2H), 4.112 (m, 2H), 3.443 (s, 3H), 2.702-2.790(m, 1H), 1.096 ¨ 1.127 (m, 6H).
Example 20: Synthesis of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropylideneamino]thiourea (0-20) Step 1: 5-(2,2-dimethoxy-1-methyl-ethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine A mixture of 24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-ol (0.4 g), Potassium hydroxide (0.158 g) and 2-bromo-1,1-dimethoxy-propane (0.4 mL)in N,N-Dimethylacetamide (4 mL)was heated at 100 C for 24 h.The mixture was cooled to ambient temperature and water (50 mL) was added and the mixture extracted with Ethyl acetate ( 2 X 30 mL). The combined organic layer was washed with a saturated solution of Sodium chloride and dried over anhydrous Sodium sulphate and evaporated under reduced pressure and the crude obtained was purified by Silica gel flash column chromatography using a gradient of Ethyl acetate/Hepatane to obtain the title compound (0.1 g, 18 %). LC/MS: Rt: 2.144 min; MS: m/z = 388.4 (M+1)+; 1H NMR (300 MHz, Chloroform-d) 8.14 (s, 2H), 7.36 (s, 3H), 7.25 (s, 2H), 7.16 (s, 1H), 3.51 (s, 2H), 3.43 (d, J = 5.7 Hz, 4H), 3.39 (t, J
= 2.8 Hz, 5H).
Step 2: 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropanal A solution of 5-(2,2-dimethoxy-1-methyl-ethoxy)-N-methyl-N44-(trifluoromethoxy)phenyl]pyrimidin-2-amine (0.1 g) and a solution of Hydrochloric acid (IN, 1 mL) was taken up in in Acetone (4 mL) and heated at 70 C for 12 h. The reaction was diluted with water (20 mL) and extracted with Ethyl acetate ( 2 X 20 mL). The combined organic layer was dried over anhydrous Sodium sulphate and evaporated under reduced pressure to get the title compound. (0.07 g, 79.4 %) LC/MS: Rt: 1.685 min; MS: m/z = 342.2 (M+1)+; 1H NMR (300 MHz, 0D0I3) 6 9.67 (s, 1H), 8.08 (s, 2H), 7.26 (dd, J =
7.5, 5.1 Hz, 2H), 7.16 (d, J = 7.9 Hz, 2H), 4.417-4.444 (m, 1H),3.43 (s, 3H), 1.59 (d, J = 7.5 Hz, 3H).
Step 3: 1-(2-isopropylpheny1)-3-[(E)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropylideneamino]thiourea The mixture of 2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropanal (0.15 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.09 g) in Ethanol (2 mL) was heated at 80 C for 1 h. The mixture was evaporated under reduced pressure and the residue subjected to Silica gel column chromatography to get the title compound (0.16 g, 68 %). LC/MS: Rt : 2.275 min; MS: m/z = 533.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.63 (s, 1H), 9.81 (s, 1H), 8.34 (s, 2H), 7.51 -7.40 (m, 2H), 7.38 (d, J = 6.3 Hz, 1H), 7.35 - 7.22 (m, 4H), 7.22 -7.11 (m, 2H), 4.97 (p, J = 6.4 Hz, 2H), 3.44 (s, 3H), 3.01 (p, J = 6.9 Hz, 2H), 1.49 (d, J = 6.3 Hz, 3H), 1.11 (dd, J
= 6.9, 2.4 Hz, 7H).
Example 21: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2424N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]oxypropylidenehydrazono]thiazolidin-4-one (C-21) A mixture of 1-(2-isopropylpheny1)-3-RE)-2424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]oxypropylideneamino]thiourea (0.1 g), Sodium acetate (0.092 g) and Methyl bromoacetate (0.076mL) in Ethanol (20 mL) was heated at 40 C for 12 h. The mixture was cooled to ambient temperature diluted with Water (50 mL) and extracted with Ethyl acetate ( 2 X
15 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate and the were evaporated invacuo and the resultant residue was subjected to flash column chromatography with Silica gel, eluting with a Ethyl acetate/Heptane gradient wo get the title compound as a yellow solid 0.108 g (70 %). LC/MS: Rt: 2.309 min; MS: m/z = 573.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 8.23 (d, J = 2.0 Hz, 2H), 7.57 (t, J = 5.4 Hz, 1H), 7.52 -7.39 (m, 4H), 7.39 -7.28 (m, 3H), 7.20 (d, J
= 7.9 Hz, 1H), 5.03 (q, J = 6.1 Hz, 1H), 4.40 - 3.93 (m, 2H), 3.44 (s, 3H), 1.42 (dd, J = 6.4, 1.7 Hz, 3H), 1.16 - 1.02 (m, 6H).
Example 22: Synthesis of 1-(2-isopropylpheny1)-3-[(E)42-methyl-344-methyl-24N-methy1-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]propylidene]amino]thiourea (0-22) Step 1: To the solution of (E)-2-methyl-344-methyl-2-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.2 g) in Ethyl acetate (5 mL) was added 10 %
Palladium on charcoal (0.02 g) and the mixture stirred under a Hydrogen atmosphere via a gas bladder for 12 h. The mixture was filtered through a Celite bed and evaporated under reduced pressure, the residue obtained subjected to flash column chromatography to afford the desired product (0.11 g). LC/MS Rt: 2.166 min; MS: m/z = 354.4 (M+1)+.
Step 2: 1-(2-isopropylpheny1)-3-REH2-methyl-3-[4-methyl-2-[N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]propylidene]amino]thiourea A mixture of 2-methyl-3-[4-methyl-2-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]propanal (0.1 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.06 g) in Ethanol (2 mL) was heated at 80 C
for 2 h. The rmixture was evaporated invacuo and the residue obtained was subjected to flash column chromatography to afford the desired product (0.13 g, 84 %) as a yellow solid. LC/MS Rt:
2.374min; MS: m/z = 545.6 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.42 (s, 1H), 9.49 (s, 1H), 8.13(s, 1H), 7.48 - 7.42 (m, 3H), 7.38 - 7.14 (m, 6H), 3.46(s, 3H), 2.91 (ddd, J =47.9, 13.5, 7.0 Hz, 2H), 2.33 (s, 3H).
Example 23: Synthesis of N-methyl-5-RE,3E)-2-methyl-3-[(3R,4R,5S,65)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxyimino-prop-1-eny1FN-[4-(trifluoromethoxy)phenyl]pyrimidin-2-amine (C-23) (E)-2-methyl-3-[24N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.17 g), 0-[(3R,4R,55,65)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]hydroxylamine (0.123 g) and Concentrated hydrochloric acid solution (1.5 mL) was taken in Ethanol (15 mL) and the mixture heated to 80 C for 48 h. The mixture was diluted with Ethyl acetate (20 mL) and the organic layer separated, dried over anhydrous Sodium sulphate, evaporated invacuo and the residue subjected to flash column chromatography on Silica gel eluting with a gradient of Ethyl acetate and n-heptane to afford the title compound (0.055 g, 18 %). LC/MS: Rt: 2.278 min; MS: m/z =
541 (M+1)+; 1H NMR
(300 MHz, DMSO-d6) 6 8.51 (s, 1H), 8.09 (s, OH), 7.68 - 7.21 (m, 2H), 6.71 (s, 1H), 5.37 (dd, J =
27.0, 2.0 Hz, 1H), 3.52 (s, 2H), 3.44 -3.36 (m, 6H), 2.03 (d, J = 1.2 Hz, 2H), 1.83 (d, J = 1.4 Hz, 1H), 1.16 (d, J = 5.9 Hz, 2H).
Example 24: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-[2-methyl-3-[4-methyl-2-[N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]propylidene]hydrazono]thiazolidin-4-one (0-24) A mixture of 1-(2-isopropylpheny1)-3-[(E)42-methyl-314-methyl-2-[N-methyl-4-(trifluoromethoxy) anilino] pyrimidin-5-yl]propylidene]amino]thiourea (0.07 g), Sodium acetate (0.063 g), Methyl bromoacetate (0.04 mL) in Ethanol (10 mL) was stirred at 40 C for 12 h. The reaction mixture was cooled to ambient temperature, diluted with Water (50 mL), Sodium hydroxide solution (1 N, 2 mL) and extracted with Ethyl acetate (2 X 50 mL). The combined organic extracts were dried over anhydrous Sodium sulphate, evaporated invacuo and the residue subjected to flash column chromatography on Silic gel, eluting with a gradient of Ethyl acetate and Heptane to obtain the title compound as a white solid 0.05 g (67 %). LC/MS: Rt: 2.409 min; MS: m/z = 585.4 (M+1)+. 1H NMR
(300 MHz, DMSO-d6) 6 8.05 (d, J = 8.2 Hz, 1H), 7.54 (dd, J = 7.6, 5.3 Hz, 1H), 7.46 (dt, J = 7.7, 3.0 Hz, 4H), 7.40 -7.23 (m, 3H), 7.27 -7.11 (m, 1H), 4.28 - 3.86 (m, 2H), 3.45 (s, 3H), 2.77 -2.61 (m, 1H), 2.27(d, J =2.5 Hz, 3H), 1.16 - 0.92 (m, 10H).
Example 25: Synthesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-3424N-methyl-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enylidene]amino]imidazolidine-2,4-dione (0-25) (E)-2-methyl-3424N-methyl-4-(trifluoromethoxy)anilino]pyrimidin-5-yl]prop-2-enal (0.227 g) and 3-amino-1-(2-isopropylphenyl)imidazolidine-2,4-dione (0.157 g) were taken up in Ethanol (10 mL. 2 drops of conc. Hydrochloric acid solution was added and the mixture heated to 80 C for 3 h. The mixture was evaporated invacuo and the residue taken up in Ethyl acetate and washed with a saturated solution of Sodium bicarbonate solution. The organic layer was separated, dried and evaporated to obtain a residue which was subjected to preparative HPLC to get the title compound (0.058 g, 13 %), LC/MS: Rt: 2.26 min; MS: m/z = 553.8 (M).
Example 26: Synthesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-3464N-methyl-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enylidene]amino]thiourea (0-26) Step 1: Synthesis of 6-chloro-N[4-(trifluoromethoxy)phenyl]pyridazin-3-amine A mixture of 3,6 Dichloro pyridazine (0.2 g) and 4-(trifluoromethoxy) aniline (0.180 g) was taken up in in Acetic acid (3 mL) and heated at 90 C for 4 h. The mixture was cooled to ambient temperature, neutralized with Sodium bicarbonate solution and extracted with Ethyl acetate. The organic layer was dried over anhydrous Sodium sulfate and concentrated under reduced pressure and the residue obtained, was purified by column chromatography using Ethyl acetate and heptane as eluent to offer the desired compound as off-white solid (0.150 g, 51 %).
LC/MS: Rt : 1.841 min;
MS: m /z = 290.25 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 9.69 (s, 1H), 7.89 ¨
7.74 (m, 2H), 7.62 (d, J = 9.3 Hz, 1H), 7.35 (d, J = 8.6 Hz, 2H), 7.22 (d, J = 9.3 Hz, 1H).
Step 2: Sythesis of 6-chloro-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine To a stirred solution of 6-chloro-N[4-(trifluoromethoxy)phenyl]pyridazin-3-amine (2.6 g) in dry DMF (35 mL) was added Sodium hydride (0.323 g) at 0 C and stirred for 10 min.
Methyl iodide (2.55 g) was added and the mixture stirred at ambient temperature for 12 h.
Saturated ammoniun chloride solution was added and the mixture extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure and the residue obtained was subjected to flash column chromatography to get the title compound as a light brown solid. (1.9 g, 70%). LC/MS: Rt : 1.996 min; MS: m/z = 304.1 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 7.55 ¨ 7.41 (m, 5H), 6.98 (d, J = 9.5 Hz, 1H), 3.47 (s, 3H).
Step 3: Sythesis of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enal A mixture of 6-bromo-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (1.8 g), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.434 g), Cesium carbonate (3.9 g), and 2-[(E)-3,3-diethoxy-2-methyl-prop-1-eny1]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3 g) was taken up in a mixture of Dioxan (4 mL) and water (16 mL) and degassed with Nitrogen gas for 10 min and subsequently heated at 95 C for 2 h. The mixture was diluted with 1N HCI
solution, neutralized with Sodium bicarbonate solution and filtered through Celite. The filtrate was extracted with Ethyl acetate and the extracts dried over anhydrous Sodium sulfate and evaporated invacuo to obtain a residue which was subjected to Silica gel flash column chromatography to obtain the desired compound as an off-white solid (1 g, 57 %). LC/MS: Rt : 2.00 min; MS: m/z =
338.5 (M+1)+; 1H
NMR (300 MHz, DMSO-d6) 5 9.63 (s, 1H), 7.63 (d, J = 9.5 Hz, 1H), 7.65 - 7.23 (m, 5H), 6.97 (d, J
= 9.5 Hz, 1H), 3.57 (s, 3H), 2.13 (d, J = 1.2 Hz, 3H).
Step 4: Sythesis of 1-(2-isopropylpheny1)-3-REH(E)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]pyridazin-3-yl]prop-2-enylidene]amino]thiourea A mixture of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enal (0.25 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.150 g) in Methanol (4 mL) was heated at 80 C for 3 h. The mixture was evaporated, Water and Ethyl acetate added and the ethyl acetate layer separated, dried evaporated invacuo to obtain a residue which was subjected to flash column chromatography to obtain the title compound as a brown solid (0.190 g, 47 %).
LC/MS: Rt : 2.256 min; MS: m/z = 529.3 (M+1,)+; 1H NMR (300 MHz, DMSO-d6) 5 11.77 (s, 1H), 9.74 (s, 1H), 7.99 (s, 1H), 7.79 - 7.44 (m, 5H), 7.37 - 7.12 (m, 2H), 6.94 (d, J = 9.5 Hz, 1H), 6.79 (s, 1H), 3.54 (s, 3H), 3.19 - 3.02 (m, 1H), 2.44 - 2.23 (m, 3H), 1.19 (d, J = 6.9 Hz, 6H).
Example 27: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-RE)-2-methyl-346-[N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]prop-2-enylidene]hydrazono]thiazolidin-4-one (0-27) A mixture of 1-(2-isopropylpheny1)-3-[(E)-RE)-2-methyl-3464N-methyl-4-(trifluoromethoxy) anilino]pyridazin-3-yl]prop-2-enylidene]amino]thiourea (0.158 g), Sodium acetate (0.049 g), and Methylbromo acetate (0.137 g) in Methanol (4 mL) was stirred for 12 h. The mixture was evaporated invacuo and the residuce was subjected to Silica gel column chromatography eluting with a gradient of Dichloromethane and methanol to obtain the title compound as a brown solid (0.09 g, 50 %). LC/MS: Rt : 2.261 min; MS: m/z = 569.90 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 8.08 (s, 1H), 7.55 -7.38 (m, 7H), 7.38 - 7.20 (m, 2H), 6.97 - 6.87 (m, 2H), 4.29 -4.04 (m, 2H), 3.54 (s, 3H), 2.90 - 2.67 (m, 1H), 2.30 (d, J = 1.2 Hz, 3H), 1.14 (t, J = 6.7 Hz, 6H).
Example 28: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxypropylidenehydrazono]thiazolidin-4-one (0-28) Step 1: Synthesis of N-methyl-6-(1-methylallyloxy)-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine To a stirred solution of 6-chloro-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (1 g) and ally! alcohol (0.475 g) in N, N-Dimethylformamide (15 mL) at 0 C was added Sodium hydride (0.160 g) and the mixture stirred at ambient temperature for 12 h. Saturated Ammonium chloride .. solution was subsequently added and the mixture extracted with Ethy acetate. The Ethyl acetate extracts were separated, dried over anhydrous Sodium sulphate and evaporated invacuo, and the residue obtained was subjected to flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to get the desired product as a brown solid (0.56 g, 50 %). LC/MS: Rt : 2.193 min; MS: m/z = 340.5 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 7.38 (s, 4H), 7.06 (d, J = 9.6 Hz, 1H), 6.96 (d, J = 9.6 Hz, 1H), 6.00 (ddd, J = 17.3, 10.6, 5.5 Hz, 1H), 5.69 (dtd, J = 7.8, 6.4, 5.1 Hz, 1H), 5.29 (dt, J = 17.3, 1.5 Hz, 1H), 5.15 (dt, J = 10.6, 1.4 Hz, 1H), 3.42 (s, 3H), 1.40 (d, J = 6.5 Hz, 3H).
Step 2: 2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxypropanal A mixture of N-methyl-6-(1-methylallyloxy)-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (0.580 g), Osmium tetroxide (0.022 g) in Water (2 mL) and Sodium periodate (1 g) was taken up in a mixture of 1,4 Dioxane (16 mL) and water (2 mL) and the mixture stirred at ambient temperature for 4 h. 2 % Sodium sulfite solution was added and the mixture extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulfate and concentrated under reduced pressure to get a solid residue which was purified by Silica gel flash column chromatography using Ethyl acetate/heptane mixture as eluent to afford the title compound. (0.32 g, 55 %). LC/MS: Rt:
1.420 min; MS: m/z = 342.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 59.65 (d, J = 1.3 Hz, 1H), 7.39 (d, J = 6.7 Hz, 5H), 7.11 (d, J = 1.7 Hz, 1H), 3.42 (s, 3H), 3.28 (d, J = 2.8 Hz, 1H), 1.44 (d, J = 7.1 Hz, 3H).
Step 3:1-(2-isopropylpheny1)-3-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxypropylideneamino]thiourea A mixture of (E)-2-methyl-3464N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]prop-2-enal (0.220 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.150 g) was taken up in Tetrahydrofuran (5 mL) and heated at 50 C for 4 h. The mixture was diluted with Water and extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was subjected to Silica gel flash column chromatography to obtain the title compound as a viscous liquid. (0.130 g, 38 %). LC/MS: Rt : 2.233 min; MS: m/z = 533.3 (M+1)+; 1H
NMR (300 MHz, DMSO-d6) 5 11.62 (s, 1H), 9.62 (s, 1H), 7.66 (d, J = 4.4 Hz, 1H), 7.47 - 6.86 (m, 11H), 5.76 (dd, J = 6.6, 4.5 Hz, 1H), 3.43 (s, 3H), 3.07 - 2.93 (m, 1H), 1.56 (d, J = 6.5 Hz, 3H), 1.15 (d, J = 6.9 Hz, 7H).
Step 4: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]
pyridazin-3-yl]oxypropylidenehydrazono]thiazolidin-4-one A mixture of 1-(2-isopropylpheny1)-3-RE)-2464N-methyl-4-(trifluoromethoxy)anilino]Pyridazine -3-yl]oxypropylideneamino]thiourea (0.160 g), Sodium acetate (0.050 g), and Methyl bromo acetate (0.138 g) in Methanol (4 mL) was stirred at ambient temperature for 12 h. The reaction mixture was subsequently diluted with Water and extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphte and evaporated invacuo and the residue subjected to Silica gel flash column chromatography to afford the title compound (0.06 g, 37 %).
LC/MS: Rt : 2.264 min;
MS: m /z = 573.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 57.55 (dd, J = 12.8, 4.1 Hz, 1H), 7.47 -7.13 (m, 9H), 7.08 (dd, J = 7.8, 1.4 Hz, 1H), 7.02 - 6.77 (m, 2H), 5.62 (ddd, J = 6.4, 4.3, 2.0 Hz, 1H), 4.36 - 3.82 (m, 2H), 3.29 (s, 3H), 2.72 -2.55 (m, 1H), 1.36 (d, J = 6.6 Hz, 3H), 0.99 (dd, J =
6.9, 1.9 Hz, 8H).
Example 29: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy) anilino]pyridazin-3-yl]oxyethylidenehydrazono]thiazolidin-4-one (0-29) Step 1: Synthesis of 6-allyloxy-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine To a stirred solution of Ally! alcohol (1 g) in N, N-Dimethylformamide (15 mL) at 0 C was added Sodium hydride (0.320 g) and the mixture stirred for 20 min. A solution of 6-chloro-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (2.7 g) in N,N-Dimethylformamide (5 mL) was added drop-wise and the mixture stirred for a further 3 h. Saturated Ammoniun chloride solution was subsequently added, the mixture extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated invacuo. The residue obtained was subjected to Silica gel flash column chromatography to obtain the title compound as a white solid (2.5 g, 86 %).
LC/MS: Rt : 2.086 min; MS: m/z = 326.25 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 57.38 (d, J = 1.5 Hz, 4H), 7.13 ¨ 6.96 (m, 2H), 6.10 (ddt, J = 17.3, 10.7, 5.5 Hz, 1H), 5.40 (dq, J = 17.3, 1.7 Hz, 1H), 5.26 (dq, J = 10.5, 1.5 Hz, 1H), 4.87 (dt, J = 5.5, 1.5 Hz, 2H), 3.43 (s, 3H).
Step 2: 2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyacetaldehyde A mixture of 6-allyloxy-N-methyl-N44-(trifluoromethoxy)phenyl]pyridazin-3-amine (0.22 g), Sodium periodate (0.434 g) and Osmium tetraoxide (catalytic) was taken up in 1,4 -Dioxane (6 mL) and Water (1 mL) and the mixture stirred at ambient temperature for 12 h. The mixture was subsequently quenched with Sodium sulfite solution and extracted with Ethyl acetate. The Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated invacuo and the residue obtained was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and n-Heptane to afford the desired compound as an off-white solid. (0.150 g, 68 %).
LC/MS: Rt : 1.382 min; MS: m/z = 328.15 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 7.45 ¨ 7.31 (m, 4H), 7.03 (q, J = 9.6 Hz, 2H), 6.40 (d, J = 7.8 Hz, 1H), 4.82 (dt, J = 7.8, 5.1 Hz, 1H), 4.21 (h, J = 5.7 Hz, 2H), 3.43 (s, 3H), 3.34 (s, 4H), 1.39 ¨ 1.25 (m, 1H), 1.24 (s, 3H).
Step 3: Synthesis of 1-(2-isopropylpheny1)-3-RE)-2464N-methyl-4-(trifluoromethoxy) anilino]
pyridazin-3-yl]oxyethylideneamino]thiourea A mixture of 2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyacetaldehyde (0.530 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.338 g) in Tetrahydrofuran (5 mL) was heated at 50 C for 3 h. The mixture was diluted with Water and extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated under reduced pressure. The residue obtained was subjected to Silica gel flash column chromatography using a gradient of Ethyl acetate and Heptane to obtain the title compound as a white solid (0.2 g, 24 %). LC/MS: Rt : 2.175 min; MS: m / z = 519.3 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 6 11.71 (s, 1H), 9.73 (s, 1H), 7.72 (t, J = 5.0 Hz, 1H), 7.39 (s, 4H), 7.37 ¨ 7.21 (m, 3H), 7.18 (dd, J = 3.7, 2.3 Hz, 2H), 7.14 ¨ 7.03 (m, 2H), 5.04 (d, J = 4.9 Hz, 2H), 3.44 (s, 3H), 3.04 (p, J = 6.9 Hz, 1H), 1.15 (d, J = 6.8 Hz, 6H).
Step 4: Synthesis of (2Z)-3-(2-isopropylpheny1)-2-[(E)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyethylidenehydrazono]thiazolidin-4-one A mixture of 1-(2-isopropylpheny1)-3-RE)-2464N-methyl-4-(trifluoromethoxy)anilino]pyridazin-3-yl]oxyethylideneamino]thiourea (0.090 g), Sodium acetate (0.029 g) and Methyl bromoacetate (0.080 g) in Tetrahydrofuran (2 mL) was stirred at ambient temperature for 12 h. The mixture was subsequently diluted with Water, extracted with Ethyl acetate, the Ethyl acetate extracts dried over anhydrous Sodium sulphate and evaporated invacuo. The resultant solid was subjected to Silica gel flash column chromatography using Ethyl acetate/Heptane gradient to obtain the title compound as a white solid (0.070 g, 57 %). LC/MS Rt : 2.189 min; MS: m/z = 559.55 (M+1)+; 1H NMR (300 MHz, DMSO-d6); 1H NMR (300 MHz, DMSO-d6) 6 7.47 (td, J = 7.9, 1.7 Hz, 3H), 7.43 ¨ 7.24 (m, 7H), 7.21 (d, J = 7.5 Hz, 1H), 7.05 (q, J = 9.3 Hz, 3H), 5.05 (d, J = 4.4 Hz, 2H), 4.31 ¨4.02 (m, 3H), 3.41 (d, J = 5.3 Hz, 12H), 2.75 (h, J = 6.8 Hz, 2H), 1.27 ¨ 1.07 (m, 9H).
Example 30: Synthesis of 1-[(E)-24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]ethylideneamino]-3-(2-isopropylphenyl)thiourea (0-30) Step 1: 5-Brom-4,6-dimethyl-pyridin-2-amine A mixture of 4,6-dimethylpyridin-2-amine (3 g) and Bromine ( 1.39 mL) taken up in Acetonitrile (30 mL) was stirred at ambient temperature for 1 h. The mixture was diluted with Water (100 mL) and the precipitate was collected by filteration and dried to afford the title product as a off white solid (3.8 g, 77%). LC/MS: Rt: 1.2 min; MS: m/z = 203 (M+1)+; 1H NMR (300 MHz, Chloroform-d) 57.28 (s, 1H), 6.37 (s, 2H), 2.43 - 2.12 (m, 6H).
Step 2: 5-bromo-4,6-dimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine A mixture of 5-Bromo-4,6-dimethyl-pyridin-2-amine (2 g), Cesium carbonate (6.46 g), 4-Trifluoromethoxy iodobenzene (4.29 g), Palladium (II) acetate (0.22 g, 0.99 mmol) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.57 g) was taken up in Toleune (40 mL) and degassed with nitrogen gas and heated at 120 C for 5 h. The reaction was diluted with Water (50 mL) and extracted with Ethyl acetate (2 X 30 mL) and the combined organic extracts were dried over anhydrous Sodium sulphate and evaporated under reduced pressure. The residue was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to obtain the title compound as an off white solid (2.7 g, 75 %).
LC/MS: Rt: 2.44 min; MS:
m/z = 363.2 (M+2)+; 1H NMR (300 MHz, CDCI3) 6 7.36 (d, J = 9.0 Hz, 2H), 7.24 (d, J = 8.8 Hz, 2H), 2.66 (s, 3H), 2.39 (s, 3H).
Step 3: 5-bromo-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine To the solution of 5-bromo-4,6-dimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine (2.5 g) in N, N-Dimethylformamide (30 mL) at 0 C was added Sodium hydride (60 %
dispersion in mineral oil, 0.415 g) portion wise. Methyl iodide (0.7 mL) was added and the mixture stirred at 0 C for 1 h.
The mixture was poured into ice water and extracted with Ethyl acetate (2 X 30 mL) and the extracts dried over anhydrous Sodium sulphate. The extracts were evaporated invacuo and the residue subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to afford the title compound as an off white solid (2.5 g, 96 %).
LC/MS: Rt: 2.628 min;
MS: m/z = 375.2 (M+2)+; 1H NMR (300 MHz, CDCI3) 57.18 (d, J = 5.3 Hz, 5H), 6.20 (s, 1H), 3.41 (s, 3H), 2.55 (d, J = 2.6 Hz, 3H), 2.16 (s, 3H).
.. Step 4: 2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]pyridin-3-ol A mixture of 5-bromo-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine (0.5 g), Tris(dibenzylideneacetone)dipalladium(0) (0.12 g), 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.057 g) and Potassium hydroxide (0.15 g) was taken up in 1,4-Dioxan (4 mL) and Water (4 mL) and heated at 90 C for 2 h. The mixture was cooled to ambient temperature and .. diluted with Water (50 mL) and extracted with Ethyl acetate (2 X 30 mL).The combined organic layer was dried over anhydrous Sodium sulphate evaporated invacuo and the residue was subjected to Silica gel flash column chromatography to get the title compound as an off white solid (0.4 g, 96%). LC/MS: Rt: 1.614 min; MS: m/z = 313.25 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 8.25 (s, 1H), 7.22 (s, 1H), 7.10 (d, J = 9.1 Hz, 1H), 6.59 (s, 1H), 3.28 (s, 3H), 2.29 (s, 3H), 2.11 (s, .. 3H).
Step 5: 5-(2, 2-diethoxyethoxy)-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl]pyridin-2-amine A mixture of 2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]pyridin-3-ol (0.3 g), Potassium hydroxide (0.27 g) and Bromoacetaldehyde diethylacetal (0.217 mL) was taken up in N,N-Dimethylacetamide (4 mL) and heated at 100 C for 1 h. The mixture was subsequently cooled to ambient temperature and Water (50 mL) was added and extracted with Ethyl acetate (2 X 20 mL).
The combined Ethyl acetate extracts were washed with brine, dried over anhydrous Sodium sulphate and evaporated invacuo to get the title compound as a pale yellow oil (0.27 g, 66 %).
LC/MS: Rt : 2.45 min; MS: m/z = 429.3 (M); 1H NMR (DMSO-d6): 1H NMR (300 MHz, DMSO-d6) 57.32 (d, J = 2.0 Hz, 4H), 6.42 (s, 1H), 4.78 (t, J = 5.1 Hz, 1H), 3.79 ¨ 3.46 (m, 5H), 2.32 (s, 4H), 2.13 (s, 3H), 1.15 (t, J = 7.0 Hz, 6H).
Step 6: 24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]acetaldehyde To the solution of 5-(2,2-diethoxyethoxy)-N,4,6-trimethyl-N44-(trifluoromethoxy)phenyl] pyridin-2-amine (0.25 g) in Acetone (5 mL) was added a solution of Hydrochloric acid (1 mL). The mixture was heated at 70 C for 2 h. The mixture was subsequently basified with sat.
Sodium bicarbonate solution and extracted with Ethyl acetate (2 X 20 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate and evaporated invacuo to get the title compound as a pale yellow oil (0.2 g, 96 %). LC/MS: Rt : 1.56 min; MS: m/z = 355 (M); 1H NMR
(DMSO-d6): 1H NMR
(300 MHz, DMSO-d6) 59.70 (s, OH), 7.32 (d, J = 5.0 Hz, 8H), 6.43 (d, J = 5.5 Hz, 1H), 5.18 (s, OH), 4.55 (s, 1H), 2.30 (d, J = 6.2 Hz, 3H), 2.17 ¨ 1.91 (m, 3H).
Step 7: 1-[(E)-24[2,4-dimethyl-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]ethylideneamino]-3-(2-isopropylphenyl)thiourea A mixture of 24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]acetaldehyde (0.15 g) and 1-amino-3-(2-isopropylphenyl)thiourea (0.09 g) in Ethanol (4 mL) was heated at 80 C
for 2 h. The mixture was evaporated under reduced pressure and the residue obtained was subjected to Silica gel flash column chromatography eluting with a gradient of Ethyl acetate and Heptane to obtain the title compound as a white solid. (0.16 g, 69 %). LC/MS:
Rt : 2.37 min; MS:
m/z = 546.3(M); 1H NMR (DMSO-d6) 5 11.69(s, 1H), 9.75(s, 1H), 7.70 (t, J = 5.4 Hz, 1H), 7.39 ¨
7.07 (m, 7H), 6.44 (s, 1H), 4.48 (d, J = 5.4 Hz, 2H), 2.34 (s, 3H), 2.15 (s, 3H), 1.14 (d, J = 6.8 Hz, 6H).
Example 31: Synthesis of (2Z)-2-[(E)-24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]ethylidenehydrazono]-3-(2-isopropylphenyl)thiazolidin-4-one (0-31) A mixture of 1-[(E)-24[2,4-dimethy1-64N-methyl-4-(trifluoromethoxy)anilino]-3-pyridyl]oxy]
ethylideneamino]-3-(2-isopropylphenyl)thiourea (0.1 g), Sodium acetate (0.09 g) and Methyl bromoacetate (0.056 mL) in Ethanol (4 mL) was stirred at 40 C for 12 h. The mixture was cooled to ambient temperature and diluted with Water (50 mL) and a solution of Sodium hydroxide (1 N, 1 mL) and extracted with Ethyl acetate (2 X 50 mL). The combined Ethyl acetate extracts were dried over anhydrous Sodium sulphate, evaporated invacuo and the residue subjected to Silica gel flash column chromatography to get the title compound as a yellow solid (0.042 g, 39 %). LC/MS: Rt:
2.41 min; MS: m/z = 586.4 (M+1)+; 1H NMR (300 MHz, DMSO-d6) 5 7.75 (s, 1H), 7.48 (s, 1H), 7.32 (s, 7H), 7.24(s, 1H), 6.42 (s, 2H), 4.67 ¨ 4.37 (m, 4H), 4.16 (d, J = 20.4 Hz, 3H), 2.28(s, 8H), 2.10 (s, 6H), 1.12 (dd, J = 6.9, 5.0 Hz, 12H).
Ii Ar)N'G (I) Table C:
No. Ar Q A G R R1 M/z Rt [min]
CH H
. NH N CH H H3C H N-NI CH3 N---µ 515 1.95 F+F
F . S
H , N-N CH3 501 1.89 11 0 NH N CH H H3C F+F S
F
. CH3 r/
. cH3..../
I. 0 NH N CH H NN CH3 555 1.99 F+F
F I S
S H /
lO N¨Nr C H3 541 1.95 F+F
F H3C j S
IC)"/
C-5 ik CH3 cH3 /.. j- 555 1.97 0 NCH3 N CH H N m/
F+F NI% ...".
F OK,s N /
el NCH3 N CH H N'( r\I CH3 529.3 2.37 F+F * S
F
C-7 . CH3 CH3 /.......?" 569.4 2.49 . 0 NCH3 N CH H
F+F N---f C H3 F
OKS
CH3 H3C H /,õP
F+F N(CH3)2 I. 0 NC H 3 C-CH H H N /
NIf -N CH3 571.4 2.498 * S
F
No. Ar Q A G R R1 M/z Rt [min]
0-9 ipo c H3 NCH3 CH H 611.9 2.576 F+F N(CH3)2 N
F NN/
OK) 0-10 ip CH3 N.....1 NCH3 N CH H N-f."-- ' 586.3 2.102 F+F O S N- 0 C-11 . CH3 0 NCH3 N CH H cH3 1 , ,N H 572.3 2.149 F+F
F 0\,,,sr 0 0-12 * C H3 F+F 568.4 2.465 N...._a NV
F
S
0 [ C H3 0-13 a H3c cH3 1-N H
H NH
N(.1( NCH3 N CH H 532.3 2.134 F+F * 0 F
C
0-14 H3cH3 0 CH H
F+F ii N N, ,j- 539 2.18 y N
C-15 a H3c C H3 H
NLNW
NCH3 CH CH H 528.75 2.396 -if C H3 F+F * S
F
C-16 cH3 F+F H
N..._,NLN4." 543.7 2.411 40 õs C H3 F
0-17 1p C H3 40 cH3 0 NCH3 N CH CH3 583.4 2.498 F+F N--INLN4"-F 0\,s C H3 No. Ar Q A G R R1 M/z Rt [min]
0-18 a H3c c H3 H H 'Ts 0 NCH3 N CH H is F+F NyN-N
519.65 2.187 F S
0-19 ip C H3 40 cH3 7-O NCH3 N CH H 559.3 2.25 F+F N--1N-N-----"/
F Od\S
0-20 0 H3c c H3 H H
0 NCH3 N CH H N N o 533.3 2.275 F+F S
0 y 'I\lc H3 F
40 cH3 wr 573.3 2.309 F+F N..,N./7-1".
F
OKS
0-22 a H3c CH3 H H
0 NCH3 N CH CH3 I.
r\j)(NNj.s 545.65 2.374 F+F S C H3 F
0-23 c H3 o-01-13 0,, 0-cH3 cH3 0 NCH3 N CH H , 541 2.3 F+F N
H3C 0 0' \
F
¨
0-24 1p cH3 0 cH3 NCH3 N CH CH3 585.4 2.409 F+F m N
F 0\._.j C-25 H3c 40 cH3 -F+F O Nre N, /.?-.µ 553.8 2.26 y 1\V
0-26 a H3c C H3 H H
WI NCH3 CH N H lei NyN`r\j 529.3 2.256 F+F
No. Ar Q A G R R1 M/z Rt [min]
40, cH3 0 NCH3 CH N H c H3 569.9 2.261 * cH3 40o NCH3 CH N H c H, 573.4 2.264 F+F 0 NrN,Nr0 cH3 40o NCH3 CH N H cH3 ¨r 559.55 2.189 F+F
NNO
F+F CH3 C-0 NCH3 CH CH3 o NNAN 546.3 2.37 H H
C-31 cH3 CH3 cH3 586.4 2.419 F+F CH3 N
Biological examples:
Example B1: Action on Yellow fever mosquito (Aedes aegypti) For evaluating control of yellow fever mosquito (Aedes aegyptt) the test unit consisted of 96-well-5 microtiter plates containing 200plof tap water per well and 5-15 freshly hatched A. aegyptilarvae.
The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5p1, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at 28 1 C, 80 5 % RH
for 2 days. Larval 10 mortality was then visually assessed.
In this test, compounds 0-1, 0-2, 0-3, 0-4, 0-5, 0-6, 0-7, 0-9, 0-12, 0-16, 0-17, 0-23, 0-27, and 0-31 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B2: Action on Orchid thrips (dichromothrIps corbettt) Dichromothrtps corbetti adults used for bioassay were obtained from a colony maintained 15 continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1:1 mixture of acetone:water (vol:vol), plus Kinetic HV at a rate of 0.01%
v/v.
Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28 C for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.
In this test, compounds C-1, 0-3, 0-5, 0-6, 0-7, 0-9, 0-12, 0-14, 0-15, 0-16, 0-17, 0-23, 0-26, 0-27, and at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B3: Action on Boll weevil (Anthonomus grandis) For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well-microtiter plates containing an insect diet and 5-10 A. grandis eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO.
Different concentrations of formulated compounds were sprayed onto the insect diet at 5 pi, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 25 + 1 C and about 75 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds C-1, 0-2, 0-3, 0-4, 0-5, 0-6, 0-7, 0-8, 0-9, 0-12, 0-14, C-15, C-16, C-17, 0-22, 0-23, 0-26, 0-27, and 0-31 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B4: Action on Silverleaf whitefly (Bemista argentifolit) (adults) The active compounds were formulated by a Tecan liquid handler in 100%
cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100%
cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10m1 glass vials. A nonionic surfactant (Kinetic ) was included in the solution at a volume of 0.01% (v/v).
The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.
Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced.
The insects were collected using an aspirator and a nontoxic Tygone tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25 C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.
In this test, compounds C-3, C-5, C-6, C-7, C-8, C-12, C-15, C-16, C-17, C-22, C-23, and C-26 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B5: Action on Tobacco budworm (Heliothis virescens) For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO.
Different concentrations of formulated compounds were sprayed onto the insect diet at 10 pi, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 28 + 1 C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds C-1, 0-2, 0-3, 0-4, 0-5, 0-6, 0-7, 0-8, 0-9, 0-10, 0-11, 0-12, C-13, C-14, 0-15, 0-16, 0-17, 0-22, 0-23, 0-24, 0-26, 0-27, 0-30, and 0-31 at 800 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B6: Action on Diamond back moth (Plutella xylostella) The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water: acetone. Surfactant (Kinetic HV) is added at a rate of 0.01%
(vol/vol).The test solution is prepared at the day of use.
Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0-100%.
In this test, compounds 0-1, 0-2, 0-3, 0-4, 0-5, 0-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, 0-15, 0-16, 0-17, 0-18, 0-19, 0-20, 0-21, 0-23, 0-24, 0-26, 0-27, 0-28, 0-29, 0-30, and C-31 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
Example B7: Action on Southern armyworm (Spodoptera eridania), 2nd instar larvae The active compounds were formulated by a Tecan liquid handler in 100%
cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100 %
cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20m1 glass vials. A nonionic surfactant (Kinetic ) was included in the solution at a volume of 0.01% (v/v).
The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.
Lima bean plants (variety Sieve) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 11 armyworm larvae were placed into the bag and the bags zipped closed.
Test plants were maintained in a growth room at about 25 C and about 20-40%
relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
In this test, compounds C-1, 0-2, 0-3, 0-4, 0-5, 0-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-15, 0-16, 0-17, 0-18, 0-19, 0-23, 0-26, 0-27, and 0-31 at 300 ppm showed at least 75 % mortality in comparison with untreated controls.
Claims (15)
1. Compounds of the formula l wherein A is N or CR A;
G is N or CR B;
R, RA, and RB are H, halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3' C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, or S(=O) m Re, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Q is NR 2, O, or S(=O) m, wherein R2 is H, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, S(=O) m Re, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RA r, wherein RA is halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rc, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, or S(=O) m Re, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, where the rings are unsubstituted or substituted with Rf;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein X is -CR x a Rxb-, -O-, -S- NR x c -CR x a=CR x b-, -CR x a Rxb-CR x a Rxb-, -O-CR x a Rxb-, -S-CR x a Rxb-, -N=CR x a-, -NR x c-CR x a Rxb-, -NR x c-C(=S)-, -N=C(S-Re)-, or -NR x c-C(=O)-;
Y is -CR y a=N-, wherein the N is bound to Z;
-NR y c -C(=O)-, wherein C(=O) is bound to Z; or -NR y c -C(=S)-, wherein C(=S) is bound to Z;
Z is a single bond;
-NR z c-C(=S)-, wherein C(=S) is bound to T;
-NR z c-C(=O)-, wherein C(=O) is bound to T;
-N=C(S-R z a)-, wherein T is bound to the carbon atom;
-O-C(=O)-, wherein T is bound to the carbon atom;
-O-C(=S)-, wherein T is bound to the carbon atom; or -NR z c-C(S-Rza)=, wherein T is bound to the carbon atom;
T is O, N or N-RT;
R11 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, C(O)-NR b Rg, C(O)-Rd, aryl, aryl-carbonyl, aryloxy-C1-C4-alkyl, hetaryl, carbonyl-hetaryl, hetaryl-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9-or 10-membered bicyclic hetaryl;
R12 is a radical of the formula A1;
wherein # indicates the point of attachment to T;
R121, R122, R123 are H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-al-kynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl-oxy, C2-C6-alkynyloxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C6-alkylcarbonlyoxy, C1-C6-haloalkylcarbonlyoxy, C1-C6-alkenylcarbonlyoxy, C3-C6-cycloalkylcarbonlyoxy, or NR b Rc, or one of R121, R122, R123 may also be oxo;
R124 is H, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, or C2-C6-alkenyloxy;
and where Rxa, Rxb, Rya are H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halo-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C(O)-OR a, C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, S(=O) m Re, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rxc, Ryc, Rzc are H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen;
RT is H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cyclo-alkoxy-C1-C4-alkyl, where the alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, S(=O) m Re, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rzc together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where in the linear C1-C6-alkylene and the linear C2-C6-alkenylene a CH 2 moiety may be replaced by a carbonyl or a C=N-R' and/or wherein 1 or 2 CH 2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Rza is H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy,C2-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, C(O)-NR b Rc, C(O)-Rd, phenyl, phenylcarbonyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rza together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where in the linear C1-C6-alkylene and the linear C2-C6-alkenylene a CH 2 moiety may be replaced by a carbonyl or a C=N-R' and/or wherein 1 or 2 CH 2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Ra, Rb and Rc independently of each other are H, C1-C6-alkyl, C1-C6-haloalkyl, alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl,C3-C6-cycloalkoxy-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C1-C6-alkylen-CN, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rd is H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Re is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or substituted with halogen, phenyl and benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rf is halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxyx-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rg, or S(=O) m Re;
Rg is halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rg, C1-C6-alkylen-CN, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, or S(=O) m Re;
Rh is halogen, OH, C1-C6-alkyl, C3-C6-cycloalkyl, or CN;
m is 0, 1, or 2;
and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
G is N or CR B;
R, RA, and RB are H, halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3' C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, or S(=O) m Re, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Q is NR 2, O, or S(=O) m, wherein R2 is H, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, S(=O) m Re, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or substituted with RA r, wherein RA is halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rc, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, or S(=O) m Re, one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, where the rings are unsubstituted or substituted with Rf;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein X is -CR x a Rxb-, -O-, -S- NR x c -CR x a=CR x b-, -CR x a Rxb-CR x a Rxb-, -O-CR x a Rxb-, -S-CR x a Rxb-, -N=CR x a-, -NR x c-CR x a Rxb-, -NR x c-C(=S)-, -N=C(S-Re)-, or -NR x c-C(=O)-;
Y is -CR y a=N-, wherein the N is bound to Z;
-NR y c -C(=O)-, wherein C(=O) is bound to Z; or -NR y c -C(=S)-, wherein C(=S) is bound to Z;
Z is a single bond;
-NR z c-C(=S)-, wherein C(=S) is bound to T;
-NR z c-C(=O)-, wherein C(=O) is bound to T;
-N=C(S-R z a)-, wherein T is bound to the carbon atom;
-O-C(=O)-, wherein T is bound to the carbon atom;
-O-C(=S)-, wherein T is bound to the carbon atom; or -NR z c-C(S-Rza)=, wherein T is bound to the carbon atom;
T is O, N or N-RT;
R11 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, C(O)-NR b Rg, C(O)-Rd, aryl, aryl-carbonyl, aryloxy-C1-C4-alkyl, hetaryl, carbonyl-hetaryl, hetaryl-C1-C4-alkyl or hetaryloxy-C1-C4-alkyl, where the rings are unsubstituted or substituted with Rg and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9-or 10-membered bicyclic hetaryl;
R12 is a radical of the formula A1;
wherein # indicates the point of attachment to T;
R121, R122, R123 are H, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-al-kynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl-oxy, C2-C6-alkynyloxy, C1-C6-alkoxy-C1-C4-alkoxy, C1-C6-alkylcarbonlyoxy, C1-C6-haloalkylcarbonlyoxy, C1-C6-alkenylcarbonlyoxy, C3-C6-cycloalkylcarbonlyoxy, or NR b Rc, or one of R121, R122, R123 may also be oxo;
R124 is H, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, or C2-C6-alkenyloxy;
and where Rxa, Rxb, Rya are H, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halo-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C(O)-OR a, C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, S(=O) m Re, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rxc, Ryc, Rzc are H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkyl, or C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen;
RT is H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cyclo-alkoxy-C1-C4-alkyl, where the alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, S(=O) m Re, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rzc together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where in the linear C1-C6-alkylene and the linear C2-C6-alkenylene a CH 2 moiety may be replaced by a carbonyl or a C=N-R' and/or wherein 1 or 2 CH 2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Rza is H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy,C2-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C4-alkyl-C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C4-alkyl-C3-C6-cycloalkoxy, C1-C4-alkyl-C3-C6-cycloalkoxy, which are unsubstituted or substituted with halogen, C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, C(O)-NR b Rc, C(O)-Rd, phenyl, phenylcarbonyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rza together with RT if present, may form C1-C6-alkylene or a linear C2-C6-alkenylene group, where in the linear C1-C6-alkylene and the linear C2-C6-alkenylene a CH 2 moiety may be replaced by a carbonyl or a C=N-R' and/or wherein 1 or 2 CH 2 moieties may be replaced by O or S and/or wherein the linear C1-C6-alkylene and the linear C2-C6-alkenylene may be unsubstituted or substituted with Rh;
Ra, Rb and Rc independently of each other are H, C1-C6-alkyl, C1-C6-haloalkyl, alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl,C3-C6-cycloalkoxy-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C1-C6-alkylen-CN, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rd is H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4-alkyl, which are unsubstituted or substituted with halogen, phenyl, or benzyl, wherein the rings are unsubstituted or substituted with Rf;
Re is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or substituted with halogen, phenyl and benzyl, wherein the rings are unsubstituted or substituted with Rf;
Rf is halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxyx-C1-C4-alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rc, C1-C6-alkylen-CN, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rg, or S(=O) m Re;
Rg is halogen, N3, OH, CN, NO 2, -SCN, -SF 5, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, tri-C1-C6-alkylsilyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkoxy-C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkoxy-C1-C4alkyl, which are unsubstituted or substituted with halogen, C(O)-OR a, NR b Rc, C1-C6-alkylen-NR b Rc, O-C1-C6-alkylen-NR b Rg, C1-C6-alkylen-CN, NH-C1-C6-alkylen-NR b Rc, C(O)-NR b Rc, C(O)-Rd, SO 2 NR b Rc, or S(=O) m Re;
Rh is halogen, OH, C1-C6-alkyl, C3-C6-cycloalkyl, or CN;
m is 0, 1, or 2;
and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof.
2. The compounds of formula l according to claim 1, wherein A is CR A and G
is N.
is N.
3. The compounds of formula l according to claim 1, wherein A is N and G is CR B.
4. The compounds of formula l according to claim 1, wherein A is N and G is N.
5. The compounds of formula l according to claim 1, wherein A is CR A and G
is CR B.
is CR B.
6. The compounds of formula l according to claim 1 to claim 5, wherein Q is
7. The compounds of formula l according to any of claim 1 to claim 6, wherein X-Y-Z-T are formulas XYZT-1 to XYZT-19 wherein denotes attachment to the 6 membered hetaryl and # denotes attachment to R11 or R12;
wherein Re, xa, xb, xy and xc are as defined in compounds of formula l.
wherein Re, xa, xb, xy and xc are as defined in compounds of formula l.
8. The compounds of formula l according to claim 1, 6, or 7, wherein A is N or CR A;
G is N or CR B;
Q is NH or NCH 3;
R is H or C1-C6-alkyl;
RA is H or N(CH 3) 2;
RB is H or CH 3;
Ar is Ar-2;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein X-Y-Z-T is selected from X-Y-Z-T-1, X-Y-Z-T-2, X-Y-Z-T-3, X-Y-Z-T-4, X-Y-Z-T, X-Y-Z-T-9, X-Y-Z-T-13, X-Y-Z-T-16, X-Y-Z-T-17, X-Y-Z-T-18, and X-Y-Z-T-19;
R11 is R11-1 or R11-10;
R12 is formula A11-1;
G is N or CR B;
Q is NH or NCH 3;
R is H or C1-C6-alkyl;
RA is H or N(CH 3) 2;
RB is H or CH 3;
Ar is Ar-2;
R1 is a moiety of formula X-Y-Z-T-R11 or X-Y-Z-T-R12; wherein X-Y-Z-T is selected from X-Y-Z-T-1, X-Y-Z-T-2, X-Y-Z-T-3, X-Y-Z-T-4, X-Y-Z-T, X-Y-Z-T-9, X-Y-Z-T-13, X-Y-Z-T-16, X-Y-Z-T-17, X-Y-Z-T-18, and X-Y-Z-T-19;
R11 is R11-1 or R11-10;
R12 is formula A11-1;
9. A composition, comprising one compound of formula l according to any of claims 1 to 8, an N-oxide or an agriculturally acceptable salt thereof.
10. The composition according to claim 9, comprising additionally a further active substance.
11. A method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound according to any one of claims 1 to 8 or the composition according to claim 9 or 10.
12. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound according to any one of claims 1 to 8 or the composition according to claim 9 or 10.
13. Seed comprising a compound according to any one of claims 1 to 8, or the enantiomers, diastereomers or salts thereof or with a composition according to claim 9 or 10, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
14. A use of a compound of the formula l according to any one of claims 1 to 8, and of an agriculturally acceptable salt thereof or of the compositions according to claim 9 or 10, for protecting growing plants from attack or infestation by invertebrate pests.
15. A method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula l according to any one of claims 1 to 8, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.
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| EP16204569.4 | 2016-12-16 | ||
| EP16204569 | 2016-12-16 | ||
| PCT/EP2017/081700 WO2018108671A1 (en) | 2016-12-16 | 2017-12-06 | Pesticidal compounds |
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| CA3045224A1 true CA3045224A1 (en) | 2018-06-21 |
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| EP (1) | EP3555050A1 (en) |
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| WO2014036056A1 (en) | 2012-08-31 | 2014-03-06 | Zoetis Llc | Crystalline forms of 1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'h-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone |
| EP3760617B1 (en) * | 2012-10-25 | 2023-03-22 | Shenyang Sinochem Agrochemicals R&D Co., Ltd. | Substituted pyrimidine compound and uses thereof |
| WO2014090918A1 (en) | 2012-12-13 | 2014-06-19 | Novartis Ag | Process for the enantiomeric enrichment of diaryloxazoline derivatives |
| CN105121416B (en) | 2013-02-14 | 2018-12-04 | 日产化学工业株式会社 | The crystalline polymorphic form and its manufacturing method of isoxazoline substituted benzamide compound |
| WO2014204622A1 (en) | 2013-06-20 | 2014-12-24 | Dow Agrosciences Llc | Improved process for the preparation of certain triaryl rhamnose carbamates |
| TWI652014B (en) | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | Heterocyclic substituted bicycloazole insecticide |
| BR112017003705B1 (en) | 2014-08-22 | 2022-07-12 | Glaxosmithkline Intellectual Property Development Limited | Tricyclic nitrogen-containing compounds for the treatment of neISSERIA GONORRHOEA infection |
| US10721933B2 (en) | 2015-01-23 | 2020-07-28 | Syngenta Participations Ag | Pesticidally active semi-carbazones and thiosemicarbazones derivatives |
| JP2018515433A (en) | 2015-03-27 | 2018-06-14 | シンジェンタ パーティシペーションズ アーゲー | Pesticide active carbamoylated and thiocarbamoylated oxime derivatives |
-
2017
- 2017-12-06 CN CN201780086330.9A patent/CN110291072A/en active Pending
- 2017-12-06 EP EP17825760.6A patent/EP3555050A1/en not_active Withdrawn
- 2017-12-06 WO PCT/EP2017/081700 patent/WO2018108671A1/en unknown
- 2017-12-06 JP JP2019531715A patent/JP2020502117A/en active Pending
- 2017-12-06 AU AU2017374992A patent/AU2017374992A1/en not_active Abandoned
- 2017-12-06 RU RU2019121534A patent/RU2019121534A/en not_active Application Discontinuation
- 2017-12-06 CA CA3045224A patent/CA3045224A1/en not_active Abandoned
- 2017-12-06 MX MX2019007120A patent/MX2019007120A/en unknown
- 2017-12-06 PE PE2019001269A patent/PE20191322A1/en unknown
- 2017-12-06 BR BR112019011211A patent/BR112019011211A2/en not_active Application Discontinuation
- 2017-12-06 KR KR1020197020183A patent/KR20190092539A/en unknown
- 2017-12-06 US US16/469,876 patent/US20200077658A1/en not_active Abandoned
-
2019
- 2019-06-11 IL IL267249A patent/IL267249A/en unknown
- 2019-06-14 CL CL2019001652A patent/CL2019001652A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN110291072A (en) | 2019-09-27 |
| IL267249A (en) | 2019-08-29 |
| AU2017374992A1 (en) | 2019-06-20 |
| PE20191322A1 (en) | 2019-09-24 |
| EP3555050A1 (en) | 2019-10-23 |
| US20200077658A1 (en) | 2020-03-12 |
| BR112019011211A2 (en) | 2019-10-15 |
| MX2019007120A (en) | 2019-09-16 |
| CL2019001652A1 (en) | 2019-08-30 |
| RU2019121534A (en) | 2021-01-18 |
| KR20190092539A (en) | 2019-08-07 |
| WO2018108671A1 (en) | 2018-06-21 |
| JP2020502117A (en) | 2020-01-23 |
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